1-Chloroethyl chloroformate → HCID 69812443, compound

Participants

Reaction Steps

To a stirred solution of (5R,7R)-4-(1′-benzyl-5-chloro-4-((isopropylamino)methyl)spiro[indoline-3,4′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (17 mg, 0.025 mmol) in dichloroethane (0.5 mL) was added 1-chloroethyl carbonochloridate (8.1 μL, 0.075 mmol) at 0° C. The reaction mixture was heated at reflux overnight. After cooling, the solvents were evaporated in vacuo. The residue was dissolved in MeOH (1 mL) and heated at reflux for 1 hour. After cooling, the solvent was evaporated in vacuo. The residue was taken up in DCM, washed with saturated aqueous NaHCO3 solution and brine, dried, and concentrated. The residue was purified by column chromatography (4% 7N ammonia in MeOH/DCM) to give (5R,7R)-4-(5-chloro-4-((isopropylamino)methyl)spiro[indoline-3,4′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (6 mg, 41%). LCMS (APCI+) m/z 591, 593 [M+H]+; Rt=2.78 min.

Provenance & Evidence