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US 8,507,673 B2Granted
Process for preparing 5,7 diaminopyrazolo [1,5-A] pyrimidine compounds
AssigneesEmory University, Imperial College of Science and Technology
InventorsDennis C. Liotta, James P. Snyder, Ashutosh S. Jogalekar, Anthony G. M. Barrett, Matthew John Fuchter, Matthew J. Cook, Sebastian H. B. Kroll
Life of this patent
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Abstract
Processes for the preparation of certain 5,7-diaminopyrazolo[1,5-α]pyrimidine compounds comprising the reaction of a primary or secondary amine and a protected 5-halo-7-aminopyrazolo[1,5-α]pyrimidine compound in solvent system comprising water and one or more organic solvents, optionally in the presence of an exogenous base.
Claims13
A process for preparing compounds of Formula I:
- or salts thereof,
- wherein
- R1 is H, halo, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, heterocyclyl, heterocyclylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, amino;
- R2 is alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, heterocyclyl, heterocyclylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, amino;
- R3 is H, alkyl, aryl, cycloalkyl;
- R4 is alkyl, alkenyl, aryl, arylalkyl, arylalkenyl, cycloalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, and heteroarylalkyl;
- comprising:
- (a) reacting a compound of Formula II:
- wherein
- R8 is C1-8 alkyl, C6-14 aryl, C7-20 arylalkyl, C4-7 heterocyclic, C5-15 heterocyclicalkyl, C4-7 heteroaryl, C5-15 heteroaralkyl, C1-8 alkoxy, C6-14 aryloxy, C7-20 arylalkoxy, C4-7 heterocyclicoxy, C5-15 heterocyclicalkoxy, C4-7 heteroaryloxy, or C5-15 heteroaralkyloxy;
- X is F, Cl, Br, or I;
- R1 is as defined above;
- and
- R2 is as defined above and is, optionally, protected with a protecting group;
- with a compound of Formula III:
- R3R4NH Formula III
- wherein
- R3 is as defined above and is, optionally, protected with a protecting group;
- R4 is as defined above and is, optionally, protected with a protecting group;
- in a solvent system comprising water and one or more organic solvents, optionally in the presence of a base;
- and
- (b) deprotecting the resulting compound to produce a compound of Formula I or a salt thereof;
- wherein each alkyl group may be optionally substituted by one or more halo, alkyl, lower alkyl, alkenyl, cycloalkyl, acyl, hydroxy, hydroxyalkyl, heterocyclic, heteroaryl, aryl, amino, aminoalkyl, —NRxRy, oxo, cyano, carboxy, carboxyalkyl, alkoxycarbonyl, —ORx, —C(O)Rx, —C(O)—NH2, —C(O)—N(H)Rx, —C(O)—N(H)O Rx, —C(O)—NRxRy, —NRyC(O)Rx, —NRyC(O)NRxRy, —OC(O)NRxRy, —NRyC(O)ORx, —S(O)n—Rx, —S(O)2—NH2, —S(O)n—N(H)Rx and/or —S(O)2—NRxRy, wherein Rx and Ry are each independently C1-6 alkyl.
20 more elements
The process of claiml, wherein the solvent system comprises a base.
Dependencies are inferred from the claim text.