4-Chlorobenzyl mercaptan → HCID 9999629, compound

Participants

Reaction Steps

Potassium tertbutoxide (318 mg, 2.84 mmol) is dissolved in anhydrous THF (5 mL) and (4-Chlorophenyl)-methanethiol (0.375 mL, 2.84 mmol) is then added and stirred for 30 min room temperature. This resulting solution is then added to a solution of crude 9 (170 mg) dissolved in anhydrous THF (3 mL). The reaction is stirred for 4 hours at room temperature and then heated to 60° C. for 18 hours. The reaction is diluted with water and extracted with a solution containing 5% methanol and 95% methylene chloride (10 mL×3). The combined organics are dried over sodium sulfate, filtered and then concentrated in vacuo. Chromatography (3% MeOH/methylene chloride) provides 3-(4-Chloro-benzylsulfanyl)-5-(pyridin-4-ylamino)-isothiazole-4-carboxylic acid amide (18 mg, 2.5%-2 steps). 1H NMR (d6 DMSO): δ 8.17 (2H, broad s), 7.45 (2H, d, J=8.4 Hz), 7.37 (2H, d, J=8.4 Hz), 6.99 (2H, broad s), 4.32 (2H, s); LRMS (M+): 376.9, (M−): 375.0.

Provenance & Evidence