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

HRID 2352878Notes

Reaction equation

HRID 2352878 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]([CH3:30])[N:25]=[C:26]([CH3:29])[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: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.CC(C)=O>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:10](=[CH:9][C:8]([C:12]([C:14]5[CH:15]=[C:16]([NH:20][C:21]([C:23]6[N:24]([CH3:30])[N:25]=[C:26]([CH3:29])[C:27]=6[Cl:28])=[O:22])[CH:17]=[CH:18][CH:19]=5)=[O:13])=[CH:7][CH:6]=4)[NH:5][C:4]3=[O:31])=[CH:41][CH:40]=2)[CH2:37][CH2:38]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 178434051HCID 178434051, compound

Product 1

HCID 1784340504-chloro-1,3-dimethyl-N-[3-[3-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]-2-oxo-1H-indole-6-carbonyl]phenyl]pyrazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 4-Chloro-2,5-dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (prepared below, 70 mg, 0.160 mmol) and THF (1.5 mL). To the resulting solution was added 4-(4-methyl-piperazin-1-yl)-phenylamine (30.6 mg, 0.160 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 acetone yielding 58% (56.7 mg, 0.093 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-abf6026e84734f59bd1563212a7e3ac2
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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