N,N-Diethyl-2-propanamine → HCID 59200054, compound

Participants

Reaction Conditions

Reaction Steps

Diethyl-iso-propylamine (1.13 mmol) is added a solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (0.75 mmol), pyrrolo[2,3-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. overnight. The reaction mixture is concentrated in vacuo. The residue is dissolved in EtOAc, washed with saturated aqueous Na2CO3 and water, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10% CH3CN in DCM to give a crude product. The crude product is crystallized from EtOAc to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrol[2,3-b]pyridine-1-ylamide (95 mg, 38%) as a solid. MS: 331 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.89 (s, 3H), 6.65 (d, H), 7.23 (m, H), 7.48-7.66 (m, 2H), 8.01-8.15 (m, 2H), 8.29 (m, H), 8.64 (d, H), 8.77 (d, H), 9.33 (s, 2H).

Provenance & Evidence