Ethanol → 5-(3-Aminophenoxy)-6-ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}pyrazine-2-carboxamide

HRID 1526171Notes

Reaction equation

HRID 1526171 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][O:22][CH2:21][CH2:20]3)=[CH:15][C:14]=2[CH3:25])=[N:5][C:4]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-])=O)[CH:28]=1)[CH3:2].C(O)C>[Pd].O1CCCC1>[NH2:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[O:26][C:4]1[N:5]=[C:6]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[CH:15][C:14]=2[CH3:25])[C:7]([C:9]([NH2:11])=[O:10])=[N:8][C:3]=1[CH2:1][CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 1176668846-Ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide

Product 1

HCID 1176671155-(3-Aminophenoxy)-6-ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}pyrazine-2-carboxamideYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6-ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (145 mg), ethanol (2 mL), and tetrahydrofuran (6 mL) was added 10% palladium-supported carbon (50% wet product) (30 mg), followed by stirring for 5 hours under a hydrogen gas atmosphere (1 atm). The reaction mixture was filtered through celite and then the solvent was evaporated under reduced pressure to obtain 5-(3-aminophenoxy)-6-ethyl-3-{[2-methyl-4-(morpholin-4-yl)phenyl]amino}pyrazine-2-carboxamide (135 mg) as a solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-70f90b5077b744eb9998a8cbd82ab961
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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