1-Methylimidazole → HCID 86687743, compound

Participants

Reaction Steps

A solution of 2-methoxy-4-(2-methoxy-4-(trifluoromethyl)phenyl)quinazoline-7-sulfonyl chloride (0.141 g, 0.326 mmol) and thiazol-2-amine (0.163 g, 1.629 mmol) in 5 mL MeCN was flooded with argon, and was treated with 1-methylimidazole (0.026 ml, 0.326 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 2-methoxy-4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)quinazoline-7-sulfonamide (0.100 g, 0.201 mmol, 61.8% yield) as an off-white solid. 1H NMR (MeCN-d3) δ: 8.26 (d, J=1.7 Hz, 1H), 7.70-7.76 (m, 1H), 7.63-7.68 (m, 1H), 7.54-7.57 (m, 1H), 7.42-7.48 (m, 2H), 7.01 (d, J=4.7 Hz, 1H), 6.64 (d, J=4.7 Hz, 1H), 4.13 (s, 3H), 3.76 (s, 3H). m/z (M+H)+=497.0.

Provenance & Evidence