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Water → HCID 178497199, compound

HRID 1243307
Notes
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Reaction equation

HRID 1243307 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[C:6](=[C:17](OCC)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]1=[O:27])(=O)C.[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]([N:38]([CH3:46])[C:39]2[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=2)=[O:37])[CH2:31][CH2:30]1.N1CCCCC1.O>CN(C)C=O>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]([N:38]([C:39]2[CH:44]=[CH:43][C:42]([NH:45]/[C:17](=[C:6]3\[C:5](=[O:27])[NH:4][C:12]4[C:7]\3=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=4)/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:41][CH:40]=2)[CH3:46])=[O:37])[CH2:31][CH2:30]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 21927707N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamideHCID 666859721-Acetyl-3-(1-ethoxy-1-phenylmethylene)-6-methoxycarbonyl-2-indolinone

Product 1

HCID 178497199HCID 178497199, compound

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

10.5 g (30.0 mmol) of 1-acetyl-3-(1-ethoxy-1-phenylmethylene)-6-methoxycarbonyl-2-indolinone (for preparation see WO 01/27081 mentioned above) and 8.60 g (33.0 mmol) N-[(4-methyl-piperazin-1-yl)-methylcarbonyl]-N-methyl-p-phenylenediamine (for preparation see WO 01/27081 mentioned above) are dissolved in 80 mL of dimethylformamide and stirred for 1 hour at 80° C. After cooling 6.50 mL of piperidine are added and the mixture is stirred for another two hours at ambient temperature. Water is added, the precipitate formed is suction filtered and washed with a little water. The residue is suspended in 200 mL of methanol, suction filtered and washed with cold water and diethyl ether. The substance is dried in vacuo at 110° C.

Workup

  1. additionare added
  2. stirringthe mixture is stirred for another two hours at ambient temperature
  3. customthe precipitate formed
  4. filtrationfiltered
  5. washwashed with a little water
  6. filtrationsuction filtered
  7. washwashed with cold water and diethyl ether
  8. customThe substance is dried in vacuo at 110° C.

Sources & evidence

ORD record
ord-01fa38e889264465aaccd3dcbf91a959
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07119093B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes