1-Methylimidazole → 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-oxoindolin-5-yl)piperidine-3-carboxamide

Participants

Reaction Steps

To a solution of 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid (100 mg, 0.24 mmol) and 5-aminoindolin-2-one (36 mg, 0.24 mmol) in dichloromethane (20 mL) were added 1-methyl-1H-imidazole (79 mg, 0.96 mmol) and EDCI (183 mg, 0.96 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 15 hours, the solid was collected by filtration and washed with methanol (4 mL) to afford 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-oxoindolin-5-yl)piperidine-3-carboxamide as a orange solid (68 mg, 51.8%). 1H NMR (300 MHz, DMSO): δ 10.31 (s, 1H), 9.87 (s, 1H), 9.67 (s, 1H), 8.86 (s, 1H), 7.68 (d, 1H, J=2.4 Hz), 7.53 (s, 1H), 7.37 (s, 1H), 7.35 (s, 1H), 6.83-6.81 (m, 1H), 6.75 (d, 1H, J=8.4 Hz), 4.82-4.67 (m, 2H), 3.71-3.65 (m, 6H), 3.48 (s, 2H), 3.12-2.95 (m, 2H), 1.98-1.74 (m, 5H). LC-MS: 546 [M+H]+, tR=1.493 min. HPLC: 98.74% at 214 nm, 98.67% at 25 4 nm, tR=3.60 min.

Provenance & Evidence