Dimethylformamide → HCID 70654224, compound

Participants

Reaction Steps

A solution of 2,3-bis(4-methoxyphenyl)quinoxaline-6-sulfonic acid (350 mg, 0.83 mmol, 1.00 equiv), thionyl chloride (1.0 g, 8.40 mmol, 10.00 equiv), N,N-dimethylformamide (60 mg, 0.82 mmol, 1.00 equiv) and toluene (10 mL) was heated to reflux for 3 h in an oil bath. The resulting mixture was concentrated in vacuo and diluted with 10 ml of dichloromethane. Then the resulting mixture was added into a solution of morpholine (1.44 g, 16.53 mmol, 20.00 equiv) in dichloromethane (10 mL) at 0° C. The reaction mixture was stirred overnight at room temperature, concentrated in vacuo, and purified by Prep-HPLC with the following conditions (AGILENT Pre-HPLC (UV-Directed)): Column, SunFire Prep C18, 5 um, 19*100 mm; mobile phase, water with 0.05% TFA and CH3CN (10% CH3CN up to 80% in 3 min, hold 80% in 2 min, up to 100% in 0.1 min, hold 100% in 0.9 min); Detector, UV 254 nm. This resulted in 60 mg (34%) of 4-(2,3-bis(4-methoxyphenyl)quinoxalin-6-ylsulfonyl)morpholine as a white solid.

Provenance & Evidence