2,6-Dichlorobenzaldehyde → 2-(2-Cyclohexylacetylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid [1-(2,6-dichlorobenzyl)-pyrrolidin-3-yl]methylamide

Participants

Reaction Steps

Compound 2-(2-cyclohexylacetylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid (1-pyrrolidin-3-yl)methylamide (1) (1.66 mmol) was dissolved in DCM (15 mL) under a blanket of nitrogen. 2,6-Dichlorobenzaldehyde (320 mg, 1.82 mmol) and sodium triacetoxyboron hydride (530 mg, 2.48 mmol) were added. The reaction mixture was stirred overnight at RT under a blanket of nitrogen. Following removal of the solvent in vacuo and purification by column chromatography (SiO2, DCM/MeOH 95:5), there were obtained 623 mg (1.11 mmol, 67% of theory) of the desired product 2-(2-cyclohexylacetylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid [1-(2,6-dichlorobenzyl)-pyrrolidin-3-yl]methylamide (K).

Provenance & Evidence