1-Chloroethyl chloroformate → HCID 44546425, compound

Participants

Reaction Steps

To a stirred solution of 9-benzenesulfonyl-5-(1-benzhydrylazetidin-3-yloxy)-3-(1-methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (238 mg, 0.37 mmol) in methanol (10 mL) at 0° C. was added a solution of 1-chloroethyl chloroformate (120 μL, 1.1 mmol) in DCM (10 mL). The reaction mixture was allowed to warm to ambient temperature then heated at 40° C. for 4 h. The reaction was cooled to ambient temperature and then concentrated in vacuo. Purification of the residue by flash chromatography (silica, 11 g column, SPE NH2, 0-20% methanol in DCM) afforded the title compound as a white solid (5 mg, 5%). 1H NMR (CDCl3 plus CD3OD, 400 MHz): 8.85 (s, 1H), 8.74-8.69 (m, 2H), 8.08 (s, 1H), 7.93 (s, 1H), 5.73-5.64 (m, 1H), 4.19-4.05 (m, 4H), 4.01 (s, 3H). LCMS (Method G): RT=5.59 min, M+H+=346.

Provenance & Evidence