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 2192276Notes

Reaction equation

HRID 2192276 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-73fce6d52a074e2d84edee7c8b16cf25
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

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