Dichloromethane → HCID 86705534, compound

Participants

Reaction Steps

To a solution of (S)-tert-butyl 2-amino-2-(3-fluoro-4-(trifluoromethyl)phenyl)ethyl(methyl)carbamate (0.220 g, 0.654 mmol) and DCM (5 mL) was cooled to 0° C. was added sequentially TEA (0.365 mL, 2.62 mmol) and CDI (0.106 g, 0.654 mmol). The reaction was stirred for 30 min then added to a solution of 138 (0.160 g, 0.654 mmol), TEA (0.365 mL, 2.62 mmol) and DCM (5 mL) at RT and the resulting solution was stirred at RT for 18 h. The solution was poured into water, and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (500:10 to 500:20) to afford 0.100 g (26.8%) of tert-butyl (S)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-2-(2-((S)-1-hydroxypropan-2-ylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)ethyl(methyl)carbamate (318).

Provenance & Evidence