1,3-Dichloro-5,5-dimethylhydantoin → 1-(4-(5-chlorothiazol-2-yl)-2-methoxyphenyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide

Participants

Reaction Steps

A solution of 1-(2-methoxy-4-(thiazol-2-yl)phenyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (0.100 g, 0.210 mmol) in 2 mL MeOH was treated with 1,3-dichloro-5,5-dimethylhydantoin (0.028 ml, 0.210 mmol) and was allowed to stir overnight at room temperature then was heated to reflux for two hours. LC/MS showed 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 1-(4-(5-chlorothiazol-2-yl)-2-methoxyphenyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (0.006 g, 0.012 mmol, 5.59% yield). 1H NMR (MeCN-d3) δ: 8.60-8.64 (m, 1H), 8.52-8.56 (m, 1H), 8.10-8.13 (m, 1H), 8.05-8.09 (m, 1H), 7.95-8.00 (m, 1H), 7.91-7.95 (m, 1H), 7.87-7.91 (m, 1H), 7.74-7.78 (m, 1H), 7.66-7.74 (m, 2H), 7.57-7.61 (m, 1H), 7.42-7.47 (m, 1H), 3.76 (s, 3H); (M+H)+=510.1.

Provenance & Evidence