Hydrazine hydrate (1:1) → 5-(3-Aminophenoxy)-6-ethyl-3-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)pyrazine-2-carboxamide

HRID 1526170Notes

Reaction equation

HRID 1526170 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]([CH2:19][N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)=[CH:15][CH:14]=2)=[N:5][C:4]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-])=O)[CH:29]=1)[CH3:2].O.NN>C(O)C.O.[Fe](Cl)Cl>[NH2:34][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=1)[O:27][C:4]1[N:5]=[C:6]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][N:20]3[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]3)=[CH:17][CH:18]=2)[C:7]([C:9]([NH2:11])=[O:10])=[N:8][C:3]=1[CH2:1][CH3:2]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1176672206-Ethyl-3-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)-5-(3-nitrophenoxy)pyrazine-2-carboxamide

Product 1

HCID 1176671465-(3-Aminophenoxy)-6-ethyl-3-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)pyrazine-2-carboxamideYield 43.7%

Reagents, catalysts & solvents 3

HCID 24458Ferrous ChlorideCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-ethyl-3-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)-5-(3-nitrophenoxy)pyrazine-2-carboxamide (112 mg) in ethanol (3 mL) and water (1 mL) were added iron chloride (III) hexahydrate (31 mg), activated carbon (60 mg), and hydrazine monohydrate (221 μL), followed by stirring at 80° C. for 2 hours. The reaction mixture was left to be cooled, and then water was added thereto. The insoluble matter was collected by filtration. To the obtained solid was added a solution in chloroform-methanol (10:1), and the insoluble matter was separated by filtration. The obtained filtrate was concentrated under reduced pressure to obtain 5-(3-aminophenoxy)-6-ethyl-3-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)pyrazine-2-carboxamide (46 mg) as a pale yellow solid.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled
  3. filtrationThe insoluble matter was collected by filtration
  4. additionTo the obtained solid was added a solution in chloroform-methanol (10:1)
  5. customthe insoluble matter was separated by filtration
  6. concentrationThe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ec63961f625a4a2c9c77dd8b95793d69
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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