Trifluoroacetic acid → HCID 9816412, compound

Participants

Reaction Steps

To a stirred solution of the benzyl carbamate intermediate (34) (1.95 g, 1 equiv.) in MeOH (20 mL) was added 10% palladium on carbon (200 mg, 10%). The solution was evacuated, placed under a H2 atmosphere (35 atm) and shaken for 5 h. The suspension was then filtered through celite and washed with MeOH. The filtrate was concentrated under reduced pressure to afford the desired amine. Following general procedure 11, to a stirred solution of this amine (100 mg, 1 equiv.) and Et3N (120 uL, 1.6 equiv.) in CH2Cl2 (5 mL) was added benzenesulfonyl chloride (82 uL, 1.2 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 (gradient elution: 10% EtOAc in hexane to 67% 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 (gradient elution: 33% EtOAc in hexane to 70% EtOAc in hexane) to afford the desired N-(1-cyano-3-pyrrolidinyl)benzenesulfonamide (35).

Provenance & Evidence