Triethylamine → HCID 66550744, compound

Participants

Reaction Steps

To a mixture of 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid (100 mg, 0.25 mmol), EDCI (70 mg, 0.37 mmol), HOBt (50 mg, 0.37 mmol) and Et3N (49 mg, 0.49 mmol) in DCM (20 mL) was bubbled ammonia until saturation. The mixture was stirred at room temperature for 3 h, then was filtered and the filtrate was concentrated to give residue which was purified by column chromatography (DCM:MeOH=50:1) to afford 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamide (22 mg, 14%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 10.13 (s, 1H), 9.37 (s, 1H), 8.88 (t, 1H, J=1.5 Hz), 8.51 (d, 1H, J=7.8 Hz), 8.10 (s, 1H), 7.98 (d, 1H, J=7.5 Hz), 7.86 (d, 1H, J=2.4 Hz), 7.58 (t, 1H, J=7.8 Hz), 7.49-7.44 (m, 2H), 7.99 (d, 1H, J=8.7 Hz), 3.82 (s, 3H), 3.77 (s, 3H). LC-MS: 408 [M+H]+, tR=1.39 min. HPLC: 97.78% at 214 nm, 97.42% at 254 nm, tR=1.39 min. LC-MS: 408 [M+H]+, tR=1.392 min. HPLC: 95.38% at 214 nm, 96.23% at 254 nm, tR=3.53 min.

Provenance & Evidence