Ammonium Chloride → HCID 117667066, compound

HRID 1526168Notes

Reaction equation

HRID 1526168 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]([CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[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].[Cl-].[NH4+].C(=O)([O-])O.[Na+]>C(O)C.O.[Zn]>[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]([CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[C:7]([C:9]([NH2:11])=[O:10])=[N:8][C:3]=1[CH2:1][CH3:2]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 117667033HCID 117667033, compound

Product 1

HCID 117667066HCID 117667066, compoundYield 54.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-ethyl-3-{[4-(1-methylpiperidin-4-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (500 mg) in ethanol (10 mL) and water (10 mL) were heated to 80° C., and zinc powder (686 mg) and ammonium chloride (561 mg) were added thereto, followed by stirring at 80° C. for 3 hours. The reaction mixture was left to be cooled, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-100:10:1) to obtain 5-(3-aminophenoxy)-6-ethyl-3-{[4-(1-methylpiperidin-4-yl)phenyl]amino}pyrazine-2-carboxamide (255 mg).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic phase was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-100:10:1)

Sources & evidence

ORD record
ord-85730f0e5df4438dafbbefdeafc2cfe5
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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