Tert-butyl (8-aminooctyl)carbamate → Methyl 4-(4-(8-(tert-butoxycarbonylamino)octylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate

Participants

Reaction Steps

To a solution of methyl 4-((4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)-2-(3-chloropropoxy)benzoate (200 mg, 0.439 mmol) in THF (2 mL) was added tert-butyl (8-aminooctyl)carbamate (118 mg, 0.483 mmol) and Hunig'sBase (230 μl, 1.318 mmol). The resulting mixture was stirred for 16 h. The mixture was diluted with DCM and washed with water, then brine. The organic layer was collected, dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by silica gel chromatography using a gradient of 20-40% EtOAc/hexanes. The product fractions were collected and the solvent removed under vacuum to give 208 mg (96%) methyl 4-(4-(8-(tert-butoxycarbonylamino)octylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate.

Provenance & Evidence