1-Methylimidazole → HCID 86687749, compound

Participants

Reaction Steps

A solution of 4-(4-(difluoromethyl)-5-fluoro-2-methoxyphenyl)quinazoline-7-sulfonyl chloride (0.334 g, 0.829 mmol) and thiazol-2-amine (0.249 g, 2.488 mmol) in 4 mL MeCN was placed under argon and was treated with 1-methylimidazole (0.081 ml, 0.829 mmol). After stirring for 3 hours at room temperature, LC/MS showed mostly product, so the reaction mixture was concentrated. Purification of the crude residue by reverse phase column chromatography [Puriflash C18 30μ, 10-100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] gave 4-(4-(difluoromethyl)-5-fluoro-2-methoxyphenyl)-N-(thiazol-2-yl)quinazoline-7-sulfonamide (0.171 g, 0.367 mmol, 44.2% yield). 1H NMR (MeCN-d3) δ: 9.42 (s, 1H), 8.52 (s, 1H), 7.96 (d, J=8.7 Hz, 1H), 7.80 (d, J=8.8 Hz, 1H), 7.38 (d, J=5.4 Hz, 1H), 7.32 (d, J=9.9 Hz, 1H), 6.93-7.24 (m, 2H), 6.64 (d, J=4.7 Hz, 1H), 3.70-3.73 (s, 3H); (M+H)+=467.0.

Provenance & Evidence