3-(Trifluoromethyl)phenyl isocyanate → N-[3-(trifluoromethyl)phenyl]-1,3,4,9-tetrahydro-2H-beta-carboline-2-carboxamide

HRID 253731

Reaction equation

HRID 253731 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1.[N:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)=[C:15]=[O:16]>CN(C)C=O.ClCCl>[F:24][C:23]([F:25])([F:26])[C:19]1[CH:18]=[C:17]([NH:14][C:15]([N:2]2[CH2:3][CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH2:1]2)=[O:16])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 107838Tetrahydro-beta-carboline

Product 1

HCID 23113599N-[3-(trifluoromethyl)phenyl]-1,3,4,9-tetrahydro-2H-beta-carboline-2-carboxamideYield 61.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3,4,9-tetrahydro-1H-β-carboline (172 mg) in dimethylformamide (5 mL) was added by a solution of 1-isocyanato-3-(trifluoromethyl)benzene (173 mg) in dichloromethane (5 mL) and stirred overnight at the room temperature. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=6:1) to give the title compound (205 mg) having the following physical data.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-9ebe548c246e451ab7c77a5d5b14032b
Source dataset
uspto-grants-2011_01
Patent number
US07872133B2

Linked notes

Loading…