Hydrazine hydrate (1:1) → HCID 11453978, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 420 mg (0.71 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 of EtOH, was added 0.10 mL (2.13 mmol, 3 eq) of hydrazine hydrate. The reaction mixture was heated to 80° C. for 3 hours, before it was partitioned between EtOAc and aqueous HCl 1N. The organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel with CH2Cl2/MeOH 95:5 afforded 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 light brown solid, MS: 461 (MH+).

Provenance & Evidence