Ethanol → 2-amino-N-(5-benzenesulfonyl-1H-indazol-3-yl)-4-(4-methyl-piperazin-1-yl)-benzamide

HRID 1640981Notes

Reaction equation

HRID 1640981 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[NH:19][C:20](=[O:37])[C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)=[CH:23][C:22]=2[N+:34]([O-])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.O.C1CCCCC=1>O1CCCC1.[Pd]>[NH2:34][C:22]1[CH:23]=[C:24]([N:27]2[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]2)[CH:25]=[CH:26][C:21]=1[C:20]([NH:19][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[CH:11]=2)[NH:15][N:14]=1)=[O:37]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 8079CyclohexeneHCID 59437077N-(5-benzenesulfonyl-1H-indazol-3-yl)-4-(4-methyl-piperazin-1-yl)-2-nitro-benzamide

Product 1

HCID 594370872-amino-N-(5-benzenesulfonyl-1H-indazol-3-yl)-4-(4-methyl-piperazin-1-yl)-benzamideYield 86.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N-(5-benzenesulfonyl-1H-indazol-3-yl)-4-(4-methyl-piperazin-1-yl)-2-nitro-benzamide (1.71 g, 3.29 mmol) was suspended in a mixture of tetrahydrofuran (17 mL), ethanol (33 mL), water (25 mL) and cyclohexene (17 mL), treated with 10% palladium on carbon and stirred under reflux. After two hours the reaction was cooled to room temperature and filtered over celite washing thoroughly with tetrahydrofuran. Evaporation of the filtrate and purification of the crude product by flash chromatography over silica gel (eluent: dichloromethane/methanol/33% NH4OH in 95:5:1 ratio) afforded 1.39 g of title compound as a yellow powder (86% yield).

Workup

  1. temperatureunder reflux
  2. filtrationfiltered
  3. washover celite washing thoroughly with tetrahydrofuran
  4. customEvaporation of the filtrate and purification of the crude product by flash chromatography over silica gel (eluent: dichloromethane/methanol/33% NH4OH in 95:5:1 ratio)

Sources & evidence

ORD record
ord-015ecb48758f4f3ba63159b99173b846
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

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