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

HRID 1843664Notes

Reaction equation

HRID 1843664 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]([NH2:19])[N:14]=3)=[CH:11][N:10]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:36]=[CH:35][C:34]([N:37]=[C:38]=[O:39])=[CH:33][CH:32]=1.[Na]>CN(C)C=O>[NH2:19][C:15]1[N:14]=[C:13]([C:12]2[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:38]([NH:37][C:34]4[CH:33]=[CH:32][C:31]([C:30]([F:29])([F:40])[F:41])=[CH:36][CH:35]=4)=[O:39])[CH:7]=[CH:6][CH:5]=3)=[N:9][N:10]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[CH:11]=2)[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 5360545SodiumHCID 671841854-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyrimidin-2-amine

Product 1

HCID 671848701-{3-[4-(2-aminopyrimidin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazol-3-yl]phenyl}-3-[4-(trifluoromethyl)phenyl]ureaYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g (2.7 mmol) of 4-[3-(3-aminophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-pyrimidin-2-amine was dissolved in 290 ml of dry dimethylformamide and 386 μl of p-trifluoromethyl-phenylisocyanate were added. The reaction was then stirred at room temperature overnight. The mixture was poured into aqueous sodium hydrogenocarbonate and extracted with dichloromethane. The organic layer was then dried over sodium sulphate and evaporated. The crude was purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 8/2), affording 800 mg (53%) of the title compound.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was then dried over sodium sulphate
  3. customevaporated
  4. customThe crude was purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 8/2)

Sources & evidence

ORD record
ord-afd1ce03e3fd4d74893f43e0487a254f
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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