4-(4-Methylpiperazin-1-yl)aniline → HCID 178462568, compound

HRID 641010Notes

Reaction equation

HRID 641010 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[C:27]([Cl:28])=[CH:26][N:25]([CH2:29][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:31].[CH3:32][N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=2)[CH2:35][CH2:34]1>C1COCC1>[CH3:32][N:33]1[CH2:34][CH2:35][N:36]([C:39]2[CH:44]=[CH:43][C:42]([NH:45][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[C:27]([Cl:28])=[CH:26][N:25]([CH2:29][CH3:30])[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:31])=[CH:41][CH:40]=2)[CH2:37][CH2:38]1

Participants

4

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 178462569HCID 178462569, compound

Product 1

HCID 178462568HCID 178462568, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 4-Chloro-1-ethyl-1H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (prepared below, 85 mg, 0.1946 mmol) and THF (2.0 mL). To the resulting solution was added 4-(4-methyl-piperazin-1-yl)-phenylamine (37.3 mg, 0.195 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 (˜50 mL) was added to the solution. The precipitate that formed was collected by filtration and washed with acetone (10 mL) to afford the title compound in 43% yield (0.051 g, 0.084 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 (˜50 mL) was added to the solution
  6. customThe precipitate that formed
  7. filtrationwas collected by filtration
  8. washwashed with acetone (10 mL)

Sources & evidence

ORD record
ord-3a28c2ecd8214043af299c9c2adf5b76
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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