Ethanol → HCID 89709225, compound

HRID 1526196Notes

Reaction equation

HRID 1526196 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]([NH2:11])=[O:10])[C:6]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][CH:22]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)[CH2:21][CH2:20]3)=[C:15]([CH3:32])[CH:14]=2)=[N:5][C:4]=1[C:33]1[CH2:34][CH2:35][NH:36][CH2:37][CH:38]=1)[CH3:2].C(O)C>[Pd].O1CCCC1>[CH2:1]([C:3]1[N:8]=[C:7]([C:9]([NH2:11])=[O:10])[C:6]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:20][CH2:21][CH:22]([N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)[CH2:23][CH2:24]3)=[C:15]([CH3:32])[CH:14]=2)=[N:5][C:4]=1[CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 117667055HCID 117667055, compound

Product 1

HCID 89709225HCID 89709225, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazine-2-carboxamide (100 mg), ethanol (3.9 mL), and tetrahydrofuran (1 mL) was reacted using a continuous hydrogenation reaction device (H-Cube (registered trademark); manufactured by ThalesNano) under the conditions of CatCart (registered trademark) 10% palladium-supported carbon (manufactured by ThalesNano), a flow rate of 1 mL/min, a temperature of 70° C., and a pressure of 1015 psi. The solvent was evaporated under reduced pressure to obtain 6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-5-(piperidin-4-yl)pyrazine-2-carboxamide (87 mg) as a yellow solid.

Workup

  1. customwas reacted
  2. customa temperature of 70° C.
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1a3a50da0a4548ce86b9c9be1266239e
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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