Ammonia → HCID 67251150, compound

Participants

Reaction Conditions

Reaction Steps

In a screw-cap vial, dissolve (±)-[4-(3-chloro-pyrazin-2-ylmethyl)-7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl]-carbamic acid isopropyl ester (30 mL, 0.073 mmol) in 1-methyl-2-pyrrolidinone (NMP) (0.5 mL) and cool to −78° C. Condense NH3 into the reaction mixture (1 mL), seal the reaction vessel, and warm to room temperature over 24 h. Heat the reaction up to 50° C. for 18 h, then at 80° C. for 72 h. Cool the reaction in a dry ice bath. Carefully open the reaction vessel and allow the liquid NH3 to evaporate. Dissolve the residue in EtOAc (50 mL) and wash the organics with water (3×20 mL). Dry the organics (MgSO4), filter, and concentrate to give 27 mg crude product as a colorless film. Purify on 4 g silica gel [50-100% EtOAc/(1:1 CH2Cl2/hexanes)] to give 8 mg (28%) of the title compound as a colorless film. LCMS 100% @ 4.23 min m/z 391 (M+H), 389 (M−H).

Provenance & Evidence