Amide compounds and method for making and using

A method for inhibiting IRAK in a subject, comprising administering to a subject in need thereof an effective amount of a compound selected from:

• I-1:
• 6-bromo-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-2:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-3:
• 5′-fluoro-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-4:
• 5′-cyano-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-5:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(pyrimidin-5-yl)picolinamide;
• I-6:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-5-yl)picolinamide;
• I-7:
• 6-(3-methyl-1H-pyrazol-5-yl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-8:
• 6-(1-methyl-1H-pyrazol-4-yl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-9:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-10:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrrol-2-yl)picolinamide;
• I-11:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrrol-3-yl)picolinamide;
• I-12:
• 5′-methyl-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-13:
• 5′-cyclopropyl-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-14:
• 5′-(2-hydroxypropan-2-yl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-15:
• 2′-methyl-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-16:
• 6′-methyl-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-17:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-(trifluoromethyl)-[2,3′-bipyridine]-6-carboxamide;
• I-18:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-2′-(trifluoromethyl)-[2,4′-bipyridine]-6-carboxamide;
• I-19:
• 5′-methoxy-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-20:
• 6′-methoxy-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-21:
• 2′-methoxy-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-22:
• 5′-isopropoxy-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-23:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-((tetrahydro-2H-pyran-4-yl)oxy)-[2,3′-bipyridine]-6-carboxamide;
• I-24:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-(2,2,2-trifluoroethoxy)-[2,3′-bipyridine]-6-carboxamide;
• I-25:
• 5′-amino-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-26:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-(methylamino)-[2,3′-bipyridine]-6-carboxamide;
• I-27:
• 5′-(cyclopropylamino)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-28:
• 5′-(isopropylamino)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-29:
• 5′-(tert-butylamino)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-30:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-((tetrahydro-2H-pyran-4-yl)amino)-[2,3′-bipyridine]-6-carboxamide;
• I-31:
• 5′-((2-methoxyethyl)amino)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-32:
• 5′-((cyclopropylmethyl)amino)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-33:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-((2,2,2-trifluoroethyl)amino)-[2,3′-bipyridine]-6-carboxamide;
• I-34:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-(methylsulfonamido)-[2,3′-bipyridine]-6-carboxamide;
• I-35:
• 5′-(dimethylamino)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-36:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-(pyrrolidin-1-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-37:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-morpholino-[2,3′-bipyridine]-6-carboxamide;
• I-38:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-(4-methylpiperazin-1-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-39:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-(methylsulfonyl)-[2,3′-bipyridine]-6-carboxamide;
• I-40:
• N6-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-5′,6-dicarboxamide;
• I-41:
• N6-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-2′,6-dicarboxamide;
• I-42:
• 2′-cyano-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-43:
• 6′-amino-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-44:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)picolinamide;
• I-45:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrrolo[3,2-b]pyridin-6-yl)picolinamide;
• I-46:
• 6-(1H-indol-5-yl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-47:
• 6-(1H-indol-6-yl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-48:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-phenylpicolinamide;
• I-49:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(m-tolyl)picolinamide;
• I-50:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(p-tolyl)picolinamide;
• I-51:
• 6-(3-methoxyphenyl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-52:
• 6-(4-methoxyphenyl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-53:
• 6-(3-cyanophenyl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-54:
• 6-(4-cyanophenyl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-55:
• 6-(3-fluorophenyl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-56:
• 6-(4-fluorophenyl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-57:
• 6-(3-aminophenyl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-58:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(3-(methylamino)phenyl)picolinamide;
• I-59:
• 6-(3-(dimethylamino)phenyl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-60:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(3-(methylsulfonamido)phenyl)picolinamide;
• I-61:
• tert-butyl 6-((1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)carbamoyl)-3′,6′-dihydro-[2,4′-bipyridine]-1′(2′H)-carboxylate;
• I-62:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-1′,2′,3′,6′-tetrahydro-[2,4′-bipyridine]-6-carboxamide;
• I-63:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(piperidin-4-yl)picolinamide;
• I-64:
• tert-butyl 6-((1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)carbamoyl)-5′,6′-dihydro-[2,3′-bipyridine]-1′(2′H)-carboxylate;
• I-65:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-1′,2′,5′,6′-tetrahydro-[2,3′-bipyridine]-6-carboxamide;
• I-66:
• 6-bromo-N-(3-(5-methoxypyridin-2-yl)-1-methyl-1H-pyrazol-4-yl)picolinamide;
• I-67:
• N-(3-(5-methoxypyridin-2-yl)-1-methyl-1H-pyrazol-4-yl)-6-(1H-pyrazol-5-yl)picolinamide;
• I-68:
• N-(3-(5-methoxypyridin-2-yl)-1-methyl-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-69:
• N-(3-(5-methoxypyridin-2-yl)-1-methyl-1H-pyrazol-4-yl)-5′-methyl-[2,3′-bipyridine]-6-carboxamide;
• I-70:
• 5′-isopropoxy-N-(3-(5-methoxypyridin-2-yl)-1-methyl-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-71:
• 5′-(isopropylamino)-N-(3-(5-methoxypyridin-2-yl)-1-methyl-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-72:
• N-(1-methyl-3-(pyrrolidin-1-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-73:
• N-(1-methyl-3-(piperidin-1-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-74:
• N-(1-methyl-3-morpholino-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-75:
• 5′-methyl-N-(1-methyl-3-(pyrrolidin-1-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-76:
• 5′-methyl-N-(1-methyl-3-(piperidin-1-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-77:
• 5′-methyl-N-(1-methyl-3-morpholino-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-78:
• 6-(3-methyl-1H-pyrazol-4-yl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-79:
• 6-bromo-N-(1-isopropyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-80:
• N-(1-isopropyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-81:
• N-(1-isopropyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-methyl-[2,3′-bipyridine]-6-carboxamide;
• I-82:
• 6-bromo-N-(1-(2-morpholinoethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-83:
• N-(1-(2-morpholinoethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-84:
• 5′-methyl-N-(1-(2-morpholinoethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-85:
• 6-bromo-N-(1-(2-(4-methylpiperazin-1-yl)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-86:
• N-(1-(2-(4-methylpiperazin-1-yl)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-87:
• 5′-methyl-N-(1-(2-(4-methylpiperazin-1-yl)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-88:
• N-(1-(2-hydroxyethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-89:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(pyridin-4-yloxy)picolinamide;
• I-90:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-91:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-2′-oxo-1′,2′-dihydro-[2,4′-bipyridine]-6-carboxamide;
• I-92:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6′-oxo-1′,6′-dihydro-[2,3′-bipyridine]-6-carboxamide;
• I-93:
• N-(1-methyl-3-(pyrazin-2-yl)-1H-pyrazol-4-yl)-5′-(2,2,2-trifluoroethoxy)-[2,3′-bipyridine]-6-carboxamide;
• I-94:
• N-(3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-95:
• N-(1-(2-methoxyethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-96:
• 2′-methoxy-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-97:
• 6′-amino-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-98:
• 6′-acetamido-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-99:
• 2′-methoxy-N-(1-methyl-3-(pyrazin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-100:
• N-(1-methyl-3-(pyrazin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-101:
• N-(1-methyl-3-(pyrazin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-102:
• 6′-acetamido-N-(1-methyl-3-(pyrazin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-103:
• 2′-(benzyloxy)-N-(1-methyl-3-(pyrazin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-104:
• N-(1-(2-(diethylamino)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-105:
• N-(1-methyl-3-(pyrazin-2-yl)-1H-pyrazol-4-yl)-5′-(2,2,2-trifluoroethoxy)-[2,3′-bipyridine]-6-carboxamide formate;
• I-106:
• N-(3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide formate;
• I-107:
• N-(1-(2-methoxyethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide formate;
• I-108:
• N-(1-(2-hydroxyethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide formate;
• I-109:
• 5-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)nicotinamide;
• I-110:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[3,4′-bipyridine]-5-carboxamide;
• I-111:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[3,3′-bipyridine]-5-carboxamide;
• I-112:
• N-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-113:
• 6-bromo-N-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-114:
• 5′-methyl-N-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-115:
• 5′-(methylsulfonamido)-N-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-116:
• N-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-117:
• N-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-3-yl)picolinamide;
• I-118:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-4-((1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)amino)pyrimidine-2-carboxamide;
• I-119:
• sodium (methyl sulfonyl)(6-((1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)carbamoyl)-[2,3′-bipyridin]-5′-yl)amide;
• I-120:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-4-(5-methylpyridin-3-yl)pyrimidine-2-carboxamide;
• I-121:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(5-methylpyridin-3-yl)pyrazine-2-carboxamide;
• I-122:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)pyrazine-2-carboxamide;
• I-123:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-3-yl)pyrazine-2-carboxamide;
• I-124:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-4-(1H-pyrazol-4-yl)pyrimidine-2-carboxamide;
• I-125:
• N-(1-(1,3-dihydroxypropan-2-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-126:
• N-(1-(1,3-dihydroxypropan-2-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-methyl-[2,3′-bipyridine]-6-carboxamide;
• I-127:
• N-(1-(1,3-dihydroxypropan-2-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-128:
• 4-((1H-pyrazol-3-yl)amino)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)pyrimidine-2-carboxamide;
• I-129:
• 4-((3-methyl-1H-pyrazol-4-yl)amino)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)pyrimidine-2-carboxamide;
• I-130:
• 5′-isopropoxy-N-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-131:
• 5′-fluoro-N-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-132:
• N-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-(trifluoromethyl)-[2,3′-bipyridine]-6-carboxamide;
• I-133:
• N6-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-5′,6-dicarboxamide;
• I-134:
• 6-(1-methyl-1H-pyrazol-4-yl)-N-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-135:
• 6-((1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)carbamoyl)-[2,3′-bipyridine]-5′-carboxylic acid;
• I-136:
• 6-(3-methyl-1H-pyrazol-5-yl)-N-(1-(oxetan-3-yl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-137:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-2-(1H-pyrazol-4-yl)pyrimidine-4-carboxamide;
• I-138:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-2-(1H-pyrazol-3-yl)pyrimidine-4-carboxamide;
• I-139:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(pyridin-4-yloxy)picolinamide formate;
• I-140:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide formate;
• I-141:
• 2′-methoxy-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide formate;
• I-142:
• 6′-amino-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide formate;
• I-143:
• 6′-acetamido-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide formate;
• I-144:
• 3′-fluoro-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide formate;
• I-145:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-3′-methyl-[2,4′-bipyridine]-6-carboxamide formate;
• I-146:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-2′-methyl-[2,4′-bipyridine]-6-carboxamide formate;
• I-147:
• 6-(6-methoxy-1H-indol-2-yl)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide formate;
• I-148:
• 6-(1-(3-chlorophenyl)-1H-pyrazol-4-yl)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide formate;
• I-149:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-methyl-[2,3′-bipyridine]-6-carboxamide formate;
• I-150:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-3-yl)picolinamide formate;
• I-151:
• 6-(furan-3-yl)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide 2,2,2-trifluoroacetate;
• I-152:
• 6-(furan-2-yl)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide 2,2,2-trifluoroacetate;
• I-153:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide formate;
• I-154:
• 6-((1H-indazol-5-yl)amino)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide formate;
• I-155:
• 6-((2H-indazol-5-yl)amino)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide formate;
• I-156:
• 6-((2-aminopyridin-4-yl)oxy)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide formate;
• I-157:
• 6-((2,5-dimethylpyridin-4-yl)amino)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide formate;
• I-158:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-((6-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)pyridin-3-yl)amino)picolinamide formate;
• I-159:
• 2′-((cyclopropylmethyl)amino)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide formate;
• I-160:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide 2,2,2-trifluoroacetate;
• I-161:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-2′-((2,2,2-trifluoroethyl)amino)-[2,4′-bipyridine]-6-carboxamide formate;
• I-162:
• N-(1-(3-methoxycyclobutyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-methyl-[2,3′-bipyridine]-6-carboxamide formate;
• I-163:
• N-(1-(3-methoxycyclobutyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide formate;
• I-164:
• 5′-methyl-N-(3-(pyridin-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-165:
• 6-(1H-pyrazol-4-yl)-N-(3-(pyridin-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl)picolinamide;
• I-166:
• 6-(1H-pyrazol-3-yl)-N-(3-(pyridin-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl)picolinamide;
• I-167:
• N-(3-(pyridin-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-168:
• N-(1-(2-methoxyethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-methyl-[2,3′-bipyridine]-6-carboxamide;
• I-169:
• N-(1-(3-methoxypropyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-methyl-[2,3′-bipyridine]-6-carboxamide;
• I-170:
• 5′-methyl-N-(1-methyl-3-(5-morpholinopyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-171:
• N-(1-methyl-3-(5-morpholinopyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-172:
• N-(1-methyl-3-(5-morpholinopyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-3-yl)picolinamide;
• I-173:
• 5′-methyl-N-(1-methyl-3-(5-(4-methylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-174:
• N-(1-methyl-3-(5-(4-methylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-175:
• N-(1-methyl-3-(5-(4-methylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-3-yl)picolinamide;
• I-176:
• 5′-methyl-N-(1-methyl-3-(5-morpholinopyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide dihydrochloride;
• I-177:
• 5′-methyl-N-(1-methyl-3-(5-(4-methylpiperazin-1-yl)pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide dihydrochloride;
• I-178:
• N-(3-(5-(2-hydroxy-2-methylpropoxy)pyridin-2-yl)-1-methyl-1H-pyrazol-4-yl)-5′-methyl-[2,3′-bipyridine]-6-carboxamide;
• I-179:
• N-(3-(5-(2-hydroxy-2-methylpropoxy)pyridin-2-yl)-1-methyl-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-180:
• N-(3-(5-(2-hydroxy-2-methylpropoxy)pyridin-2-yl)-1-methyl-1H-pyrazol-4-yl)-6-(1H-pyrazol-3-yl)picolinamide;
• I-181:
• 5′-methyl-N-(1-methyl-3-(5-(oxetan-3-yloxy)pyridin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide;
• I-182:
• N-(1-methyl-3-(5-(oxetan-3-yloxy)pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-183:
• N-(1-methyl-3-(5-(oxetan-3-yloxy)pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-3-yl)picolinamide;
• I-184:
• N-(3-(3,5-difluoropyridin-2-yl)-1-((1r,4r)-4-ethoxycyclohexyl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-185:
• 3′-fluoro-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-186:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-3′-methyl-[2,4′-bipyridine]-6-carboxamide;
• I-187:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-2′-methyl-[2,4′-bipyridine]-6-carboxamide;
• I-188:
• 6-(6-methoxy-1H-indol-2-yl)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-189:
• 6-(1-(3-chlorophenyl)-1H-pyrazol-4-yl)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-190:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-methyl-[2,3′-bipyridine]-6-carboxamide;
• I-191:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-3-yl)picolinamide;
• I-192:
• 6-(furan-3-yl)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-193:
• 6-(furan-2-yl)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-193:
• 6-(furan-2-yl)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-194:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-195:
• 6-((1H-indazol-5-yl)amino)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-196:
• 6-((2H-indazol-5-yl)amino)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-197:
• 6-((2-aminopyridin-4-yl)oxy)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-198:
• 6-((2,5-dimethylpyridin-4-yl)amino)-N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)picolinamide;
• I-199:
• N-(1-(2-(2-methoxyethoxy)ethyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-((6-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)pyridin-3-yl)amino)picolinamide;
• I-200:
• 2′-((cyclopropylmethyl)amino)-N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-201:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-[2,4′-bipyridine]-6-carboxamide;
• I-202:
• N-(1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-2′-((2,2,2-trifluoroethyl)amino)-[2,4′-bipyridine]-6-carboxamide;
• I-203:
• N-(1-(3-methoxycyclobutyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-5′-methyl-[2,3′-bipyridine]-6-carboxamide;
• I-204:
• N-(1-(3-methoxycyclobutyl)-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-205:
• N-(1-((1r,4r)-4-ethoxycyclohexyl)-3-(pyrazin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• I-206:
• N-(1-((1r,4r)-4-ethoxycyclohexyl)-3-(pyrazin-2-yl)-1H-pyrazol-4-yl)-5′-methyl-[2,3′-bipyridine]-6-carboxamide;
• I-207:
• N-(1-methyl-3-(pyrazin-2-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)picolinamide;
• or
• I-208:
• 5′-methyl-N-(1-methyl-3-(pyrazin-2-yl)-1H-pyrazol-4-yl)-[2,3′-bipyridine]-6-carboxamide.

A method for inhibiting an IRAK protein, comprising contacting the IRAK protein with an effective amount of a compound according to formula 1

• or a salt thereof, wherein:
• ring A is heterocyclyl;
• R1 is H, aliphatic, or heteroaliphatic;
• R2 is H, aliphatic, heteroaliphatic, or heterocyclyl;
• each of Z1, Z2, Z3, and Z4, independently is N or CR3, wherein at least one of Z1, Z2, Z3, and Z4 is N;
• each R3 independently is H, aliphatic, or heteroaliphatic;
• and
• R4 is halogen, heterocycloaliphatic, aromatic, —O-aromatic, or —NH-aromatic.