Benzene, 2-isocyanato-1-methoxy-4-(trifluoromethyl)- → 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-(1-pyridin-4-ylmethyl-1H-benzoimidazol-4-yl)-urea

HRID 1515320Notes

Reaction equation

HRID 1515320 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([NH2:17])[C:11]=3[N:10]=[CH:9]2)=[CH:3][CH:2]=1.[N:18]([C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:22]=1[O:31][CH3:32])=[C:19]=[O:20]>CN(C)C=O.ClCCl>[CH3:32][O:31][C:22]1[CH:23]=[CH:24][C:25]([C:27]([F:30])([F:29])[F:28])=[CH:26][C:21]=1[NH:18][C:19]([NH:17][C:16]1[C:11]2[N:10]=[CH:9][N:8]([CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1)=[O:20]

Participants

4

Reactant 2

HCID 11983909Benzene, 2-isocyanato-1-methoxy-4-(trifluoromethyl)-HCID 594286291-(Pyridin-4-yl)methyl-1H-benzimidazol-4-ylamine

Product 1

HCID 498059681-(2-Methoxy-5-trifluoromethyl-phenyl)-3-(1-pyridin-4-ylmethyl-1H-benzoimidazol-4-yl)-urea

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Compound 3d (75 mg, 0.334 mmol) is dissolved in dimethylformamide/dichloromethane (1:4, 5.0 mL) and 2-isocyanato-1-methoxy-4-trifluoromethyl-benzene (1.0 equiv., 73 mg, 0.334 mmol) is added at room temperature and allowed to react for 16 hours under nitrogen atmosphere. All solvent is then removed on a rotary evaporator and toluene (3×25 mL) is added and stripped off to remove residual dimethylformamide. The crude solid is then triturated using ethyl ether, and the resulting solid is then filtered and dried yielding title compound as a white solid.

Workup

  1. customto react for 16 hours under nitrogen atmosphere
  2. customAll solvent is then removed on a rotary evaporator and toluene (3×25 mL)
  3. additionis added
  4. customto remove residual dimethylformamide
  5. customThe crude solid is then triturated
  6. filtrationthe resulting solid is then filtered
  7. customdried

Sources & evidence

ORD record
ord-ccc96746136c4d25b46015b9c2915a6e
Source dataset
uspto-grants-2012_07
Patent number
US08222421B2

Reaction notes

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