Process for the preparation of N,N-dicyclopropyl-4-(1,5-dimethyl-1H-pyrazol-3-ylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

A process for the preparation of Compound I of the formula

• comprising the steps of
• a) reacting Compound 1 of the formula
• with a halogenating agent, such as NBS, in a suitable solvent to afford Compound 2 of the formula
• wherein X is Cl, Br or I;
• b) reacting Compound 2 with an alcohol to afford Compound 3 of the formula
• wherein
• R is Me, Et, iPr, nPr, nBu, sec-Bu or tBu;
• and
• X is as defined above;
• c) subsequently reacting Compound 3 with a nitrating agent to afford Compound 4 of the formula
• d) reacting Compound 4, first, with an ethylating agent to afford Compound 5 of the formula
• wherein
• R and X are as defined above;
• and subsequently with a suitably substituted imidazole of the formula,
• wherein
• Y is H, Cl, Br, I or B(OR′)2;
• and
• R′ is Me, Et, i-Pr, n-Pr, n-Bu, sec-Bu, t-Bu, —(CH2)n or —C(Me)2C(Me)2-;
• and
• n is 2, 3, 4 or 5;
• in the presence of a suitable catalytic metal, a ligand, an inorganic salt and optionally an organic base, to afford Compound 6 of the formula
• e) which is then reacted with hydrogen in the presence of a suitable catalytic metal and optionally a base, to afford Compound 7 of the formula
• wherein R is as defined above;
• f) which is reacted with Compound 24 of the formula
• wherein Z is Cl, Br, I, —OP(O)(OR″)2 or —OS(O)CF3;
• in the presence of a suitable metal, a ligand, and base, to afford Compound 26 of the formula
• wherein R″ is Ph or t-Bu and M is Li, Na, K, Cs, Rb, Mg or Ca;
• g) which is reacted with Compound 27 of the formula
• in a the presence of a suitable activator, a suitable solvent, such as DCM, and optionally a base, to afford Compound I.