Trifluoroacetic acid → HCID 10515827, compound

Participants

Reaction Steps

Following general procedure 11, to a stirred solution of the amine (30) (109 mg, 1 equiv.) and Et3N (130 uL, 1.7 equiv.) in CH2Cl2 (7 mL) was added benzenesulfonyl chloride (97 uL, 1.4 equiv.). The resultant mixture was stirred at rt for 16 h. The mixture was then diluted with EtOAc and washed successively with 10% citric acid, H2O and brine. The organic extract was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (50% EtOAc in hexane) to afford the desired coupled product. The N-Boc group of the coupled product was then converted to the cyanamide (N—CN) following general procedure 3 (i.e. successive treatment with TFA and BrCN). The crude material was purified by flash chromatography (50% EtOAc in hexane) to afford the desired N-[(1-cyano-3-pyrrolidinyl)methyl]benzenesulfonamide (31).

Provenance & Evidence