Diisopropylethylamine → 2-{4-(2-(Azetidin-1-yl)-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyanopyridin-4-yl)phenoxy}ethyl N2,N6-bis(tert-butoxycarbonyl)-L-lysyl-L-alaninate

Participants

Reaction Steps

32.73 mg (0.094 mmol) of N2,N6-bis(tert-butoxycarbonyl)-L-lysine were initially charged in 1.5 ml of DMF. 19.8 mg (0.103 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 17.4 mg (0.129 mmol) of 1-hydroxy-1H-benzotriazole hydrate and 55.5 mg (0.429 mmol) of N,N-diisopropylethylamine were added, and the mixture was then stirred at RT for 15 min, 64 mg (0.086 mmol) of 2-{4-(2-(azetidin-1-yl)-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyanopyridin-4-yl)phenoxy}ethyl L-alaninate trifluoroacetate (Example 45) were then added and the mixture was stirred at RT overnight. The crude product was purified by preparative HPLC (acetonitrile/water+0.1% TFA). This gave 76 mg (92% of theory) of the target compound.

Provenance & Evidence