Nitrogen → HCID 178446037, compound

Participants

Reaction Steps

660 mg (1 mmol) of 1-(1,3-benzothiazol-2-yl)cyclopentyl(1S)-1-[cyano(triphenylphosphoranylidene)acetyl]pentylcarbamate was dissolved in 25 mL of dichloromethane and ozone was passed through the solution at −78° C. for 15 min. The reaction was quenched with N2 for 5 min before 79 mg (0.95 mmol) of 3-aminopyrazole in 4 mL of tetrahydrofuran was added. The reaction was allowed to warm to room temperature over 1 h. Solvent was removed and the residue was redissolved in 5 mL of tetrahydrofuran. 1 mL of 1 M silver nitrate in water was added and the reaction was stirred at room temperature overnight. Water was added and the mixture was extracted with ether (4×). The ether layer was washed with brine (3×) and dried over magnesium sulfate. After removal of solvent, purification by silica gel column chromatography eluting with hexane:ethyl acetate (1:2) gave 150 mg (32%) of 1-(1,3-benzothiazol-2-yl)cyclopentyl(1S)-1-[oxo(1H-pyrazol-3-ylamino)acetyl]pentylcarbamate as a solid. 1H-NMR (400 MHz CDCl3) δ 7.87 (d, J=8 Hz, 1H), 7.66 (d, J=8 Hz, 1H), 7.42 (s, 1H), 7.36 (t, J=8 Hz, 1H), 7.22 (m, 2H), 6.78 (s, 1H), 4.96 (br, 1H), 2.45 (m, 4H), 1.86 (m, 4H), 1.30 (m, 6H), 0.88 (t, J=8 Hz, 3H). ES-LCMS m/z 469 (M+H). C23H27N3O4S: 0.34 EtOAc: 0.13 H2O: Anal C 58.3%, H 5.93%, N 13.95%; Calcd C, 58.3%, H, 6.02%, N, 13.95%.

Provenance & Evidence