Acetyl chloride → HCID 86687781, compound

Participants

Reaction Steps

A solution of 2-methoxy-4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)quinazoline-7-sulfonamide (Example 511; 0.075 g, 0.151 mmol) in 5 mL MeOH was treated with acetyl chloride (0.215 ml, 3.02 mmol) and was allowed to stir overnight at room temperature. An additional portion of acetyl chloride (0.215 ml, 3.02 mmol) was added, and the reaction mixture was heated to 100° C. for one hour. LC/MS showed mostly product, so the reaction mixture was concentrated. Purification of the crude residue by reverse phase column chromatography [Puriflash C18, 30μ, 55 g, 10-100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] gave 4-(2-methoxy-4-(trifluoromethyl)phenyl)-2-oxo-N-(thiazol-2-yl)-1,2-dihydroquinazoline-7-sulfonamide (0.055 g, 0.114 mmol, 75% yield) as an off-white solid. 1H NMR (MeCN-d3) δ: 7.80 (s, 1H), 7.43-7.55 (m, 5H), 7.39 (d, J=8.4 Hz, 1H), 7.02 (d, J=4.7 Hz, 1H), 6.66 (d, J=4.7 Hz, 1H), 3.78 (s, 3H); (M+H)+=483.0.

Provenance & Evidence