Trifluoroacetic acid → HCID 22601268, compound

Participants

Reaction Steps

Following general procedure 11, to a stirred solution of the amine (56) (256 mg, 1 equiv.) and Et3N (0.31 mL, 1.5 equiv.) in CH2Cl2 (5 mL) was added dibenzo[b,d]furan-2-sulfonyl chloride (356 mg, 0.9 equiv.). The resultant mixture was stirred at rt for 30 min. 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 (gradient elution: 20% EtOAc in hexane to 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 washed with ether to afford the desired yellow solid N-(1-cyano-3-azetidinyl)dibenzo[b,d]furan-2-sulfonamide (58).

Provenance & Evidence