N,N-Diethyl-2-propanamine → 2-Pyridin-2-yl-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide

Participants

Reaction Conditions

Reaction Steps

Diethyl-iso-propylamine (3.54 mmol) is added a solution of 2-pyridin-2-yl-pyrimidine-5-carboxylic acid HCl (1.18 mmol), 5-methanesulfonyl-indol-1-ylamine (1.18 mmol) and TBTU (1.77 mmol) in anhydrous DMF (16 mL) at rt. The reaction mixture is stirred at 90° C. overnight and then concentrated in vacuo. The residue is dissolved in EtOAc (50 mL) and water (50 mL). The organic layer is separated, washed with water (2×20 mL) and brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue is triturated with EtOAc and DCM to afford 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide (125 mg, 27%) as a solid. MS: 394 (M+H); 1H NMR (300 MHz, CD3OD): δ 3.14 (s, 3H), 6.82 (m, H) 7.50-7.72 (m, 3H), 7.80 (m, H), 8.07 (m, H), 8.30 (m, 2H), 8.70(d, H), 8.80 (s, H), 9.51 (s, 2H).

Provenance & Evidence