2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → 1-(2-Fluoro-5-trifluoromethyl-phenyl)-3-[4-(2-pyridin-4-yl-imidazol-1-yl)-phenyl]-urea

HRID 1864728Notes

Reaction equation

HRID 1864728 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)[CH:9]=[CH:10][N:11]=2)=[CH:3][CH:2]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1[N:30]=[C:31]=[O:32]>C(Cl)Cl.CN(C=O)C>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1[NH:30][C:31]([NH:18][C:15]1[CH:16]=[CH:17][C:12]([N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[CH:13][CH:14]=1)=[O:32]

Participants

5

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 579747254-(2-Pyridin-4-yl-imidazol-1-yl)-phenylamine

Product 1

HCID 115394681-(2-Fluoro-5-trifluoromethyl-phenyl)-3-[4-(2-pyridin-4-yl-imidazol-1-yl)-phenyl]-urea

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-Pyridin-4-yl-imidazol-1-yl)-phenylamine (100 mg, 0.424 mmol) in DCM (4.0 mL) and DMF (1.0 mL) is added 1-fluoro-2-isocyanato-4-trifluoromethyl-benzene (91 mg, 0.445 mmol, 1.05 equiv) and allowed to stir for 2 h at RT. All solvent is then removed under reduced pressure and the resulting solid was purified by column chromatography (5% MeOH:95% DCM) to afford 1-(2-Fluoro-5-trifluoromethyl-phenyl)-3-[4-(2-pyridin-4-yl-imidazol-1-yl)-phenyl]-urea as an off-white solid.

Workup

  1. customAll solvent is then removed under reduced pressure
  2. customthe resulting solid was purified by column chromatography (5% MeOH:95% DCM)

Sources & evidence

ORD record
ord-683608173af847b18ad514afe5b04415
Source dataset
uspto-grants-2009_12
Patent number
US07625931B2

Reaction notes

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