Tert-Butylamine → 7-[(3r)-3-[(Tert-butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-n-(tert-butyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxamide

Participants

Reaction Steps

To a solution of the product (33 mg, 0.061 mmol) from Example 3, Step B, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC; 12 mg, 0.063 mmol), 1-hydroxybenzotriazole (HOBt; 9 mg, 0.067 mmol) and N,N-diisopropylethyl amine (0.026 mL, 0.15 mmol) in 1.0 mL of dichloromethane was added tert-butylamine (0.011 mL, 0.100 mmol). The solution was stirred at room temperature for 18 h. The reaction mixture was subjected directly to flash chromatography (silica gel; 35 to 75% ethyl acetate/hexanes step-gradient elution) to afford the title compound as a white foam.

Provenance & Evidence