1-Methylimidazole → HCID 66549517, compound

Participants

Reaction Steps

To a solution of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (80 mg, 0.22 mmol) and 6-(methoxycarbonyl)nicotinic acid (39 mg, 0.22 mmol) in dichloromethane (15 mL) was added the solution of 1-methyl-1H-imidazole (71 mg, 0.88 mmol) and EDCI (164 mg, 0.88 mmol) in dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 15 hours, the solid was collected by filtration and washed with MeOH to afford methyl 5-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)picolinate (90 mg, 80.3%) as a off-white solid. 1H NMR (300 MHz, DMSO): δ 9.57 (s, 1H), 9.07 (s, 1H), 8.99 (d, 1H, J=6.3 Hz), 8.79 (s, 1H), 8.36 (dd, 1H, J1=8.1 Hz, J2=2.1 Hz), 8.11 (d, 1H, J=8.1 Hz), 7.86 (s, 1H), 7.45 (s, 1H), 6.90 (d, 1H, J=8.7 Hz), 4.60-4.58 (m, 1H), 3.89 (s, 3H), 3.75 (s, 3H), 3.71 (s, 3H), 3.64 (brs, 4H), 2.28-2.24 (m, 1H), 2.11-2.06 (m, 1H). LC-MS: 536 [M+H]+, tR=1.37 min. HPLC: 95.95% at 214 nm, 96.44% at 254 nm, tR=4.85 min.

Provenance & Evidence