1-Chloroethyl chloroformate → HCID 69060680, compound

Participants

Reaction Steps

A stirred mixture of 5-(4-benzylpiperazin-1-yl)-3-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine (0.865 g, 2.00 mmol) and 1-chloroethylchloroformate (0.65 mL, 6.00 mmol) in 1,2-dichloroethane is heated at reflux temperature for 2.5 h under nitrogen, cooled and concentrated in vacuo, and reconcentrated from CH2Cl2 to a solid. This solid is heated with ethanol at reflux temperature under nitrogen for 2 h, cooled and concentrated in vacuo. The resultant residue is stirred in ethanol for 16 h and filtered. The filtercake is heated with methanol and two drops of concentrated hydrochloric acid for 30 h and concentrated in vacuo to a solid. This solid is chromatographed (silica gel, 5:95 concentrated ammonium hydroxide:ethanol as eluent) to afford the free amine of the title compound as a white solid. The free amine is dissolved in methanol, treated with 2.0 M aqueous hydrochloric acid (1.1 mL, 2.2 mmol) and concentrated to an off-white solid residue. This residue is recystallized from methanol to afford the title compound as an off-white solid, 165 mg (24% yield), mp 198-203° C. (foams), identified by NMR and mass spectral analyses.

Provenance & Evidence