Ethanol → HCID 66643208, compound

HRID 869281Notes

Reaction equation

HRID 869281 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:16]=[C:17]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([N:33]4[CH2:38][CH2:37][CH:36]([N:39]5[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]5)[CH2:35][CH2:34]4)=[C:29]([CH3:46])[CH:28]=3)[C:18]([C:23]([NH2:25])=[O:24])=[N:19][C:20]=2[CH2:21][CH3:22])[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)C>[OH-].[Pd+2].[OH-].C(O)(=O)C>[CH2:21]([C:20]1[N:19]=[C:18]([C:23]([NH2:25])=[O:24])[C:17]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][CH:36]([N:39]4[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]4)[CH2:35][CH2:34]3)=[C:29]([CH3:46])[CH:28]=2)=[N:16][C:15]=1[NH:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH3:22]

Participants

5

Reactant 2

HCID 702EthanolHCID 66642829HCID 66642829, compound

Product 1

HCID 66643208HCID 66643208, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

To a mixture of 5-[(1-benzylpiperidin-4-yl)amino]-6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (Example 507) (1.31 g), ethanol (26 mL) and acetic acid (13 mL), palladium hydroxide (0.65 g) was added and stirred under a hydrogen atmosphere at room temperature for 3 days. After the catalyst was separated by filtration, the solvent was concentrated and partitioned using chloroform and saturated aqueous sodium hydrogen carbonate. The organic layer was concentrated to give 6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-5-(piperidin-4-ylamino)pyrazine-2-carboxamide (0.73 g) as a light yellow solid.

Workup

  1. additionwas added
  2. customAfter the catalyst was separated by filtration
  3. concentrationthe solvent was concentrated
  4. custompartitioned
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-93a14c1422d745fda4bed2fec75cd042
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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