4-(4-Methylpiperazin-1-yl)aniline → HCID 178426930, compound

HRID 640962Notes

Reaction equation

HRID 640962 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][C:13]3[CH:14]=[C:15]([NH:19][C:20]([C:22]4[N:23]([CH3:28])[N:24]=[C:25]([CH3:27])[CH:26]=4)=[O:21])[CH:16]=[CH:17][CH:18]=3)=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:29].[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][C:40]([NH2:43])=[CH:39][CH:38]=2)[CH2:33][CH2:32]1>C1COCC1>[CH3:30][N:31]1[CH2:32][CH2:33][N:34]([C:37]2[CH:42]=[CH:41][C:40]([NH:43][CH:2]=[C:3]3[C:11]4[C:6](=[CH:7][C:8]([CH2:12][C:13]5[CH:14]=[C:15]([NH:19][C:20]([C:22]6[N:23]([CH3:28])[N:24]=[C:25]([CH3:27])[CH:26]=6)=[O:21])[CH:16]=[CH:17][CH:18]=5)=[CH:9][CH:10]=4)[NH:5][C:4]3=[O:29])=[CH:39][CH:38]=2)[CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 178426931HCID 178426931, compound

Product 1

HCID 178426930HCID 178426930, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indol-6-ylmethyl)-phenyl]-amide (prepared below, 50 mg, 0.129 mmol) and THF (1 mL). To the resulting solution was added 4-(4-methyl-piperazin-1-yl)-phenylamine (24.6 mg, 0.129 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 ˜3 mL of i-prOH yielding 35% (25.3 mg, 0.045 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-9fb3581c1e3149caa9e4bebab30ddc75
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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