HCID 117666838, compound → HCID 117667067, compound

HRID 1526218Notes

Reaction equation

HRID 1526218 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]([CH3:46])[C:14]2[N:15]=[C:16]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH2:37][CH2:36][CH:35]([N:38]5[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]5)[CH2:34][CH2:33]4)=[C:28]([CH3:45])[CH:27]=3)[C:17]([C:22]([NH2:24])=[O:23])=[N:18][C:19]=2[CH2:20][CH3:21])[CH2:9]1)C1C=CC=CC=1>[OH-].[Pd+2].[OH-].C(O)C>[CH2:20]([C:19]1[N:18]=[C:17]([C:22]([NH2:24])=[O:23])[C:16]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:37][CH2:36][CH:35]([N:38]4[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]4)[CH2:34][CH2:33]3)=[C:28]([CH3:45])[CH:27]=2)=[N:15][C:14]=1[N:13]([CH3:46])[C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH3:21]

Participants

4

Reactant 1

HCID 117666838HCID 117666838, compound

Product 1

HCID 117667067HCID 117667067, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-{[(3R)-1-benzylpyrrolidin-3-yl](methyl)amino}-6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (60 mg), and ethanol (21 mL) was reacted using a continuous hydrogenation reaction device (H-Cube (registered trademark); manufactured by ThalesNano) under the conditions of CatCart (registered trademark) 20% palladium hydroxide-supported carbon (manufactured by ThalesNano), a flow rate of 1 mL/min, a temperature of 50° C., and a pressure of 290 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-{methyl[(3R)-pyrrolidin-3-yl]amino}pyrazine-2-carboxamide (38 mg) as a yellow solid.

Workup

  1. customwas reacted
  2. customa temperature of 50° C.
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7d4120aaeb5a4984aa762bf26f8d6820
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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