4-(Trifluoromethyl)phenyl isocyanate → 1-(3-{1-(4-methoxybenzyl)-4-[2-(methylamino)pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)-3-[4-(trifluoromethyl)phenyl]urea

HRID 1843653Notes

Reaction equation

HRID 1843653 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[CH:14]=3)=[CH:11][N:10]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:37]=[CH:36][C:35]([N:38]=[C:39]=[O:40])=[CH:34][CH:33]=1.[Na]>CN(C)C=O>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:10]2[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[CH:14]=3)[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:39]([NH:38][C:35]4[CH:34]=[CH:33][C:32]([C:31]([F:30])([F:41])[F:42])=[CH:37][CH:36]=4)=[O:40])[CH:7]=[CH:6][CH:5]=3)=[N:9]2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 5360545SodiumHCID 671862484-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-methylpyridin-2-amine

Product 1

HCID 671843231-(3-{1-(4-methoxybenzyl)-4-[2-(methylamino)pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)-3-[4-(trifluoromethyl)phenyl]ureaYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

250 mg (0.65 mmol) of 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-N-methylpyridin-2-amine were dissolved in 10 ml of dry dimethylformamide and 92 μl of p-trifluoromethyl-phenylisocyanate were added. The reaction was stirred at room temperature overnight, poured into aqueous sodium hydrogenocarbonate and extracted with dichloromethane. The organic phase was then dried over sodium sulphate and evaporated. The residue was purified by flash-chromatography on a silica gel column CH2Cl2-CH3COCH3; from 9/1 to 8/2), giving 234 mg (63%) of the title compound.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was then dried over sodium sulphate
  3. customevaporated
  4. customThe residue was purified by flash-chromatography on a silica gel column CH2Cl2-CH3COCH3

Sources & evidence

ORD record
ord-84c55cc751ab47cb894f55b76fcbf212
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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