4-(4-Methylpiperazin-1-yl)aniline → HCID 178426954, compound

HRID 641008Notes

Reaction equation

HRID 641008 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[CH:27]=[C:26]([CH3:28])[N:25]([C:29]([CH3:32])([CH3:31])[CH3:30])[N:24]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:33].[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([C:41]2[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=2)[CH2:37][CH2:36]1>C1COCC1>[CH3:34][N:35]1[CH2:36][CH2:37][N:38]([C:41]2[CH:46]=[CH:45][C:44]([NH:47][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[CH:27]=[C:26]([CH3:28])[N:25]([C:29]([CH3:32])([CH3:30])[CH3:31])[N:24]=6)=[O:22])[CH:17]=[CH:18][CH:19]=5)=[O:13])=[CH:9][CH:10]=4)[NH:5][C:4]3=[O:33])=[CH:43][CH:42]=2)[CH2:39][CH2:40]1

Participants

4

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 178426965HCID 178426965, compound

Product 1

HCID 178426954HCID 178426954, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 1-tert-Butyl-5-methyl-1H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (prepared below, 179 mg, 0.4027 mmol) and THF (4 mL). To the resulting solution was added 4-(4-methyl-piperazin-1-yl)-phenylamine (77.2 mg, 0.404 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 solid residue was redissolved in EtOAc (5 mL) and Hexane (˜40 mL) was added to the solution. The precipitate that formed was collected by filtration and washed with 0° C. iPrOH (10 mL) to afford the title compound in 38% yield (0.0945 g, 0.153 mmol).

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe solid residue was redissolved in EtOAc (5 mL)
  5. additionHexane (˜40 mL) was added to the solution
  6. customThe precipitate that formed
  7. filtrationwas collected by filtration
  8. washwashed with 0° C. iPrOH (10 mL)

Sources & evidence

ORD record
ord-41085151e401498cb8a9ece85698eaca
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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