Triethylamine → HCID 11784810, compound

Participants

Reaction Steps

To a suspension of (6-Methoxy-quinazolin-4-yl)-[3-methyl-4-(piperidin-4-yloxy)-phenyl]-amine hydrochloride (150 mg, 0.251 mmol) in N,N-dimethylformamide (1.5mL) was added triethylamine (143 μL, 1.03 mmol) and cyclopentyl isocyanate (0.343 mmol). The reaction was stirred at room temperature overnight The reaction was then filtered through a 0.45 μm PTFE membrane filter and purified by preparatory HPLC. 36.3 mg of 4-[4-(6-Methoxy-quinazolin-4-ylamino)-2-methyl-phenoxy]-piperidine-1-carboxylic acid cyclopentylamide was isolated. 1H NMR (300 MHz, DMSO d6) δ 9.505 (s, 1H), 8.436 (s, 1H), 7.904 (d, J=0.9 Hz, 1H), 7.707 (d, J=3.0 Hz, 1H), 7.498-7.458 (dd, J=9.0, 3.0 Hz, 1H), 7.571-7.513 (m, 2H), 7.045 (d, J=3.0 Hz, 1H), 6.28 (d, J=2.3 Hz, 1H), 4.564-4.514 (m, 1H), 3.962-3.894 (m, 1H), 3.950 (s, 3H), 3.677-3.599 (m, 2H), 3.246-3.163 (m, 2H), 2.216 (s, 3H), 1.928-1.863 (m, 2H), 1.862-1.751 (m, 2H) 1.671-1.518 (m, 4H), 1.517-1.365 (m, 4H).

Provenance & Evidence