4-(4-Methylpiperazin-1-yl)aniline → 4-chloro-1-methyl-N-[3-[3-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]-2-oxo-1H-indole-6-carbonyl]phenyl]pyrazole-5-carboxamide

HRID 640951Notes

Reaction equation

HRID 640951 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[CH:26][C:27]=4[Cl:28])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].[CH3:31][N:32]1[CH2:37][CH2:36][N:35]([C:38]2[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=2)[CH2:34][CH2:33]1>C1COCC1>[CH3:31][N:32]1[CH2:33][CH2:34][N:35]([C:38]2[CH:43]=[CH:42][C:41]([NH:44][CH:2]=[C:3]3[C:11]4[C:6](=[CH:7][C:8]([C:12]([C:14]5[CH:15]=[C:16]([NH:20][C:21]([C:23]6[N:24]([CH3:29])[N:25]=[CH:26][C:27]=6[Cl:28])=[O:22])[CH:17]=[CH:18][CH:19]=5)=[O:13])=[CH:9][CH:10]=4)[NH:5][C:4]3=[O:30])=[CH:40][CH:39]=2)[CH2:36][CH2:37]1

Participants

4

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 1784818394-chloro-N-[3-[3-(hydroxymethylidene)-2-oxo-1H-indole-6-carbonyl]phenyl]-1-methylpyrazole-5-carboxamide

Product 1

HCID 1784807144-chloro-1-methyl-N-[3-[3-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]-2-oxo-1H-indole-6-carbonyl]phenyl]pyrazole-5-carboxamideYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 4-Chloro-2-methyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (prepared below, 100 mg, 0.240 mmol) and THF (2 mL). To the resulting solution was added 4-(4-methyl-piperazin-1-yl)-phenylamine (50.53 mg, 0.264 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was dissolved in EtOAc. The resulting solution was diluted with Hexanes to initiate the precipitation of the product. The solid precipitate that formed was filtered then washed with ˜1 mL of i-prOH yielding 32% (45 mg, 0.076 mmol) of the title compound.

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude residue was dissolved in EtOAc
  5. additionThe resulting solution was diluted with Hexanes
  6. customthe precipitation of the product
  7. customThe solid precipitate that formed
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-dc8040bc46084e9ab5fba23267eeff60
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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