Ethanol → 5-(3-Aminophenoxy)-6-isopropyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide

HRID 1526169Notes

Reaction equation

HRID 1526169 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[C:16]([C:34]([NH2:36])=[O:35])=[N:17][C:18]([C:31]([CH3:33])=[CH2:32])=[C:19]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=4)[N:20]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C(O)C>[Pd].O1CCCC1>[NH2:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[O:21][C:19]1[N:20]=[C:15]([NH:14][C:11]2[CH:10]=[CH:9][C:8]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)=[CH:13][CH:12]=2)[C:16]([C:34]([NH2:36])=[O:35])=[N:17][C:18]=1[CH:31]([CH3:32])[CH3:33]

Participants

5

Reactant 2

HCID 702EthanolHCID 1176672673-{[4-(4-Methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)-6-(prop-1-en-2-yl)pyrazine-2-carboxamide

Product 1

HCID 1176670485-(3-Aminophenoxy)-6-isopropyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamideYield 65.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)-6-(prop-1-en-2-yl)pyrazine-2-carboxamide (1.13 g), ethanol (60 mL), and tetrahydrofuran (30 mL) was added 10% palladium-supported carbon (53% wet product) (1.23 g), followed by stirring for 6 hours under a hydrogen gas atmosphere (4 atm). The reaction mixture was filtered through celite and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=100:1:0.1-30:1:0.1) to obtain 5-(3-aminophenoxy)-6-isopropyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (702 mg) as a yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=100:1:0.1-30:1:0.1)

Sources & evidence

ORD record
ord-e2a4246e2b4e4006822447ea3191dc10
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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