1-Methylimidazole → HCID 66549331, compound

Participants

Reaction Steps

To a solution of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (100 mg, 0.27 mmol) and 1H-indazole-5-carboxylic acid (44 mg, 0.27 mmol) in dichloromethane (20 mL) were added the solution of 1-methyl-1H-imidazole (88 mg, 1.1 mmol) and EDCI (206 mg, 1.1 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 15 hours, the solid formed during the reaction was collected by filtration and washed with MeOH to afford N-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-1H-indazole-5-carboxamide (78 mg, 56.1%) as a off-white solid. 1H NMR (300 MHz, DMSO): δ 13.25 (s, 1H), 9.58 (s, 1H), 8.81 (s, 1H), 8.61 (d, 1H, J=6.3 Hz), 8.36 (s, 1H), 8.19 (s, 1H), 7.88-7.86 (m, 2H), 7.56 (d, 1H, J=8.7 Hz), 7.50 (s, 1H), 6.91 (d, 1H, J=8.4 Hz), 4.61-4.59 (m, 1H), 3.73 (s, 3H), 3.65 (s, 3H), 3.62 (brs, 3H), 2.28-2.09 (m, 2H). LC-MS: 517 [M+H]+, tR=1.34 min. HPLC: 95.89% at 214 nm, 97.39% at 254 nm, tR=4.52 min

Provenance & Evidence