Triethylamine → (R)-Tetrahydrofuran-3-yl((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate

Participants

Reaction Steps

To a solution of 2-(4-((S)-3-(aminomethyl)piperidin-1-yl)-7-methylquinazolin-2-yl)phenol (210 mg, 0.6 mmol) in DMF at 0° C. were added (R)-tetrahydrofuran-3-yl chloroformate (0.09 g, 0.6 mmol) and triethylamine (167 μL, 1.2 mmol) simultaneously. Ten to fifteen minutes after addition, the reaction was complete, and quenched with water, extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give (R)-tetrahydrofuran-3-yl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate (150 mg, 54%). LC/MS: m/z 463.5 (M+H)+ at 2.37 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.41-8.43 (m, 1H), 7.86 (d, J=8.5 Hz, 1H), 7.65 (s, 1H), 7.33-7.44 (m, 3H), 6.90-6.95 (m, 2H), 5.11 (dd, J=6.2, 4.6 Hz, 1H), 4.38 (t, J=14.5 Hz, 2H), 3.68-3.79 (m, 3H), 3.60-3.63 (m, 1H), 3.28-3.31 (m, 1H), 2.98-3.07 (m, 3H), 2.50 (s, 3H), 2.06-2.15 (m, 1H), 1.85-1.91 (m, 4H), 1.70 (d, J=12.9 Hz, 1H), 1.24-1.37 (m, 1H) ppm.

Provenance & Evidence