N,N-Diethyl-2-propanamine → 2-Pyridin-3-yl-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide

Participants

Reaction Conditions

Reaction Steps

Diethyl-iso-propylamine (3.84 mmol) is added a solution of 2-pyridin-2-yl-pyrimidine-5-carboxylic acid hydrochloride (1.28 mmol), 5-methanesulfonyl-indol-1-ylamine (1.28 mmol) and TBTU (1.92 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 (60 mL), and washed with water (2×30 mL) and brine (20 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 purified by silica gel chromatography eluting with 0-5% MeOH in DCM to afford 2-pyridin-3-yl-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide (125 mg, 25%) as a solid. MS: 394 (M+H); 1H NMR (300 MHz, CDCl3): δ 3.10 (s, 3H), 6.61 (m, H) 6.98 (m, H), 7.34 (s, H), 7.51 (m, H), 7.91 (s, H), 8.83 (m, 2H), 9.49 (s, H), 9.77 (s, H), 10.10 (s, N—H).

Provenance & Evidence