1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(3-(3-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-6-yl)phenyl)urea

HRID 240868Notes

Reaction equation

HRID 240868 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[NH2:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:30]=[C:29]3[C:25]([C:26]([C:39]4[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=4)=[CH:27][N:28]3[C:31]3[N:36]=[CH:35][N:34]=[C:33]([NH:37][CH3:38])[CH:32]=3)=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:30]=[C:29]4[C:25]([C:26]([C:39]5[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=5)=[CH:27][N:28]4[C:31]4[CH:32]=[C:33]([NH:37][CH3:38])[N:34]=[CH:35][N:36]=4)=[CH:24][CH:23]=3)[CH:17]=2)=[O:10])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 509920026-(6-(3-aminophenyl)-3-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

Product 1

HCID 509920031-(4-chloro-3-(trifluoromethyl)phenyl)-3-(3-(3-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-6-yl)phenyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Chloro-4-isocyanato-2-(trifluoromethyl)benzene (15.8 mg, 0.071 mmol) was added to a mixture solution of 6-(6-(3-aminophenyl)-3-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (20 mg, 0.047 mmol) in THF (1 mL) at room temperature. After stirring at room temperature for 12 hours, the reaction solution was concentrated under reduced pressure. The residue was purified by chromatography (silica gel, EA:Hx=1:1; DCM:MeOH=100:1; 20:1). The target compound was obtained as yellow solid.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customThe residue was purified by chromatography (silica gel, EA:Hx=1:1; DCM:MeOH=100:1; 20:1)
  3. customThe target compound was obtained as yellow solid

Sources & evidence

ORD record
ord-773a5539c73a40ebaf75f47119537b20
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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