Triethylamine → HCID 71208127, compound

Participants

Reaction Steps

A 10 mL round bottom flask was charged with 3,5-difluorobenzoyl chloride (78.0 mg, 0.442 mmol) and anhydrous methylene chloride (5 mL) and was treated with 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (49.8 mg, 0.175 mmol), triethylamine (87.1 mg, 0.12 mL, 0.861 mmol), and catalytic N,N-(dimethylamino)pyridine (DMAP) (one spatula tip). The flask was capped with a glass stopper and the reaction stirred at room temperature over the weekend. The reaction was partitioned between methylene chloride (25 mL) and water (25 mL). The organic portions were dried over magnesium sulfate, filtered and rinsed with methylene chloride, concentrated on a rotary evaporator, and briefly dried on a vacuum pump. The material was then purified via Analogix Intelliflash 280 chromatography using a 12 g silica gel column and a 1%-5% MeOH/CH2Cl2 gradient elution. Two columns were required to isolate the desired product from the bis-acylation side product. Fractions containing the two products were separately combined and concentrated. The second product to elute was the desired product N-(7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-3,5-difluoro-benzamide, isolated as an off-white solid (44 mg, 60%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.91 (t, J=5.14 Hz, 1H) 8.27 (d, J=8.66 Hz, 1H) 8.03 (s, 1H) 7.38-7.73 (m, 9H) 6.90 (d, J=1.81 Hz, 1H) 4.37 (d, J=5.24 Hz, 2H).

Provenance & Evidence