Ammonia → HCID 178483951, compound

HRID 2109025Notes

Reaction equation

HRID 2109025 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[C:6](=[C:14](Cl)[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[CH:26]=[CH:25][N:24]=[CH:23]3)=[CH:17][CH:16]=2)[C:5]1=[O:28])(=O)C.[CH3:29][N:30]([CH2:32][C:33]([N:35]([CH3:43])[C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=1)=[O:34])[CH3:31].C(N(CC)CC)C.N>CN(C)C=O.O.CO>[CH3:31][N:30]([CH2:32][C:33]([N:35]([C:36]1[CH:37]=[CH:38][C:39]([NH:42]/[C:14](=[C:6]2\[C:5](=[O:28])[NH:4][C:12]3[C:7]\2=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=3)/[C:15]2[CH:16]=[CH:17][C:18]([CH2:21][N:22]3[CH:26]=[CH:25][N:24]=[CH:23]3)=[CH:19][CH:20]=2)=[CH:40][CH:41]=1)[CH3:43])=[O:34])[CH3:29]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 22569697N-(4-aminophenyl)-2-(dimethylamino)-N-methylAcetamideHCID 690618881-Acetyl-3-(1-chloro-1-(4-(imidazol-1-yl-methyl)-phenyl)-methylene)-6-chloro-2-indolinone

Product 1

HCID 178483951HCID 178483951, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

0.7 g of 1-acetyl-3-(1-chloro-1-(4-(imidazol-1-yl-methyl)-phenyl)-methylene)-6-chloro-2-indolinone (educt X.1), 0.4 g of N-(dimethylamino-methylcarbonyl)-N-methyl-p-phenylenediamine (educt XV.125) and 1.2 ml of triethylamine are dissolved in 10 ml of dimethylformamide and stirred for 15 hours at 60° C. After cooling, 10 ml of methanol and 2 ml concentrated ammonia are added and the mixture is stirred for a further three hours at ambient temperature. Water is added and the mixture is extracted with ethyl acetate. The organic phase is washed three times with water, dried over sodium sulphate and concentrated in the rotary evaporator. The residue is purified through a silica gel column with methylene chloride/methanol/ammonia 10:1:0.1 as eluant.

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture is stirred for a further three hours at ambient temperature
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic phase is washed three times with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in the rotary evaporator
  7. customThe residue is purified through a silica gel column with methylene chloride/methanol/ammonia 10:1:0.1 as eluant

Sources & evidence

ORD record
ord-86a6a76682bc4c53a82faf60ffc8d0e8
Source dataset
uspto-grants-2009_04
Patent number
US07514468B2

Reaction notes

Loading…