Ammonia → HCID 71623053, compound

HRID 1526184Notes

Reaction equation

HRID 1526184 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:17]([C:32]([NH2:34])=[O:33])=[N:18][CH:19]=[C:20]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)[N:21]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1.[N:35]1C=CC=C[CH:36]=1.N.C(=O)([O-])O.[Na+]>CO.C(Cl)(Cl)Cl>[C:36]([C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:17]([C:32]([NH2:34])=[O:33])=[N:18][CH:19]=[C:20]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)[N:21]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]1)#[N:35]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 516892Sodium BicarbonateHCID 89709221HCID 89709221, compound

Product 1

HCID 71623053HCID 71623053, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of 3-{[3-bromo-4-(4-methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (645 mg) and pyridine (3.87 mL) was added cuprous cyanide (219 mg), followed by heating and refluxing for 5 hours. Cuprous cyanide (328 mg) was further added thereto, followed by heating and refluxing for 15 hours. The reaction mixture was left to be cooled, and then a mixed solvent (10:1:0.1) of chloroform:methanol:28% aqueous ammonia was added thereto. A saturated aqueous sodium hydrogen carbonate solution was further added thereto, followed by stirring, and then the insoluble matter was separated by filtration. The filtrate was subjected to liquid separation, and then the organic phase was dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: chloroform:methanol:28% aqueous ammonia=1:0:0-20:1:0.1) to obtain 3-{[3-cyano-4-(4-methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (68 mg) as a yellow solid.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 5 hours
  3. temperatureby heating
  4. temperaturerefluxing for 15 hours
  5. waitThe reaction mixture was left
  6. temperatureto be cooled
  7. customthe insoluble matter was separated by filtration
  8. customThe filtrate was subjected to liquid separation
  9. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  10. customThen, the solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (eluent: chloroform:methanol:28% aqueous ammonia=1:0:0-20:1:0.1)

Sources & evidence

ORD record
ord-834e0aa5a6b6442cad51730a4b2d8358
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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