Triethylamine → HCID 24968984, compound

Participants

Reaction Steps

Oxalyl chloride in DCM (2 M, 1.5 mL) is added to a solution of 2-phenyl-pyrimidine-5-carboxylic acid (200 mg, 2 mmol) in DCM (20 mL) and stirred at rt for 2 h. The reaction solution is concentrated in vacuo. The residue is dissolved in DCM (20 mL). N-amino-indoline (268 mg, 2 mmol) and triethylamine (404 mg, 4 mmol) are added and stirred at rt overnight. The mixture is concentrated in vacuo and the residue is purified by silica gel column chromatography eluting with 0-40% EtOAc in heptane to afford 2-phenyl-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide (195 mg, 31%) as a solid. MS: 317 (M+H); 1H NMR (300 MHz, CD3OD): δ 3.07 (t, 2H), 3.77 (t, 2H), 6.76 (m, H), 6.82-6.95 (m, H) 7.09-7.24 (m, 2H), 7.54-7.63 (m, 3H), 8.52 (d, 2H), 9.28 (s, 2H) and 2-phenyl-pyrimidine-5-carboxylic acid (indol-1-yl)-amide (10 mg, 2%). MS: 315 (M+H). IC50=2 nM.

Provenance & Evidence