Hydrazine → HCID 11453978, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 420 mg (0.7 mmol) of (RS,SR)-2-{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-ylmethyl}-isoindole-1,3-dione in 50 mL EtOH at RT, was added 0.1 mL (2.1 mmol, 3 eq) hydrazine. The reaction mixture was heated at 80° C. over 3 hours 30 minutes. After cooling down, the reaction was quenched with a 1M solution of HCl, and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel (CH2Cl2/MeOH 95/5) yielded 210 mg (64%) of (RS,SR)-C-{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-yl}-methylamine as a light brown powder, MS: 461 (MH+).

Provenance & Evidence