1-Methylimidazole → HCID 86687737, compound

Participants

Reaction Steps

A solution of 4-(2-methoxy-4-(trifluoromethyl)phenyl)-2-methylquinazoline-7-sulfonyl chloride (Intermediate QQQQQ; 0.210 g, 0.504 mmol) and thiazol-2-amine (0.252 g, 2.52 mmol) in 5 mL MeCN was flooded with argon, and was treated with 1-methylimidazole (0.040 ml, 0.504 mmol). After stirring for 2 hours, 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-methyl-N-(thiazol-2-yl)quinazoline-7-sulfonamide (0.160 g, 0.333 mmol, 66.1% yield) as an off-white solid. 1H NMR (MeCN-d3) δ: 8.39 (d, J=1.7 Hz, 1H), 7.86 (dd, J=8.7, 1.8 Hz, 1H), 7.70 (d, J=8.7 Hz, 1H), 7.52-7.57 (m, 1H), 7.44-7.50 (m, 2H), 7.01 (d, J=4.7 Hz, 1H), 6.63 (d, J=4.7 Hz, 1H), 3.75 (s, 3H), 2.85 (s, 3H); (M+H)+=481.0.

Provenance & Evidence