Ethanol → HCID 178440136, compound

HRID 869274Notes

Reaction equation

HRID 869274 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:10]=[C:11]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)=[CH:24][CH:23]=3)[C:12]([C:18]([NH2:20])=[O:19])=[N:13][C:14]=2[C:15]([CH3:17])=[CH2:16])[CH2:4][CH2:3]1.C(O)C>[Pd].C1COCC1>[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:10]=[C:11]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)=[CH:24][CH:23]=3)[C:12]([C:18]([NH2:20])=[O:19])=[N:13][C:14]=2[CH:15]([CH3:16])[CH3:17])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 702EthanolHCID 178440135HCID 178440135, compound

Product 1

HCID 178440136HCID 178440136, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-[(trans-4-hydroxycyclohexyl)amino]-6-isopropenyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (Example 342) (205 mg), ethanol (20 mL) and THF (10 mL), 10% palladium on carbon (100 mg) was added under a hydrogen atmosphere and stirred at room temperature for 18 hours. After the catalyst was separated by filtration, the solvent was distilled off, and the residue was purified by basic silica gel column chromatography (eluent: chloroform). The resulting yellow solid was washed with ethyl acetate to give 5-[(trans-4-hydroxycyclohexyl)amino]-6-isopropyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (136 mg) as a yellow solid.

Workup

  1. additionwas added under a hydrogen atmosphere
  2. customAfter the catalyst was separated by filtration
  3. distillationthe solvent was distilled off
  4. customthe residue was purified by basic silica gel column chromatography (eluent: chloroform)
  5. washThe resulting yellow solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-ceb662908e97471ca3ba917cef80d3b4
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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