Diisopropylethylamine → 2-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-alaninate

Participants

Reaction Steps

218 mg (1.15 mmol) of N-(tert-butoxycarbonyl)-L-alanine were initially charged in 5 ml of DMF. 240 mg (1.254 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 240 mg (1.568 mmol) of 1-hydroxy-1H-benzotriazole hydrate and 0.455 ml (2.613 mmol) of N,N-diisopropylethylamine were added, 300 mg (0.523 mmol) of 2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)-6-(pyrrolidin-1-yl)pyridine-3,5-dicarbonitrile (Example 1) were then added and the mixture was stirred at RT overnight. The reaction mixture was purified by preparative HPLC (acetonitrile/water+0.1% TFA). This gave 382 mg (98% of theory) of the target compound.

Provenance & Evidence