1-Chloroethyl chloroformate → (R)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-((2-nitrophenyl)sulfonyl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-6-benzyl-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-((2-nitrophenyl)sulfonyl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (1.17 g, 1.47 mmol) in MeCN (15 mL) was added 1-chloroethyl carbonochloridate (0.18 mL, 1.62 mmol), and the mixture was stirred for 15 minutes at which time the mixture was concentrated in vacuo. The resulting residue was dissolved in a 2:1 mixture of dichloromethane:methanol (15 mL) and heated at 40° C. for 1 hour and then placed at room temperature for ca. 15 h. The mixture was then diluted with dichloromethane and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined dried over Na2SO4, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (3-12% MeOH/DCM) to provide (R)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-((2-nitrophenyl)sulfonyl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 702.3 (M+H)+.

Provenance & Evidence