N,N-Diethyl-2-propanamine → 4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrol[3,2-b]pyridine-1-ylamide

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Reaction Conditions

Reaction Steps

Diethyl-iso-propylamine (1.88 mmol) is added a solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (0.75 mmol), pyrrolo[3,2-b]pyridine-1-ylamine (0.75 mmol) and TBTU (0.9 mmol) in anhydrous DMF (7 mL) at rt, and the reaction mixture is stirred at 80° C. for 8 h. The reaction mixture is concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-10% MeOH in DCM to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrol[3,2-b]pyridine-1-ylamide (155 mg, 63%) as a solid. MS: 331 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.89 (s, 3H), 7.01 (d, H), 7.64-7.77 (m, 2H), 8.15 (m, H), 8.25 (m, H), 8.59-8.76 (m, 3H), 8.82 (d, H), 9.31 (s, 2H). IC50=13 nM.

Provenance & Evidence