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Cesium carbonate → 6-Ethyl-3-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)-5-(3-nitrophenoxy)pyrazine-2-carboxamide

HRID 1526167
Notes
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Reaction equation

HRID 1526167 reaction equation
Cl[C:2]1[C:3]([C:20]([NH2:22])=[O:21])=[N:4][C:5]([CH2:18][CH3:19])=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:7]=1.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=2)[CH2:26][CH2:25]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH2:18]([C:5]1[N:4]=[C:3]([C:20]([NH2:22])=[O:21])[C:2]([NH:35][C:34]2[CH:33]=[CH:32][C:31]([CH2:30][N:27]3[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]3)=[CH:37][CH:36]=2)=[N:7][C:6]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 897091113-Chloro-6-ethyl-5-(3-nitrophenoxy)pyrazine-2-carboxamide

Product 1

HCID 1176672206-Ethyl-3-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)-5-(3-nitrophenoxy)pyrazine-2-carboxamide
Yield 18.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Under an argon atmosphere, a mixture of 3-chloro-6-ethyl-5-(3-nitrophenoxy)pyrazine-2-carboxamide (50 mg), 4-[(4-methylpiperazin-1-yl)methyl]aniline (48 mg), tris(dibenzylideneacetone)dipalladium (0) (14 mg), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (30 mg), cesium carbonate (101 mg), and dioxane (2 mL) was heated and refluxed for 4 hours. The reaction mixture was cooled and then diluted with ethyl acetate, and the organic phase was washed with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate:methanol:28% aqueous ammonia=95:4.5:0.5-90:9:1, chloroform: methanol=1:0-9:1) to obtain 6-ethyl-3-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}amino)-5-(3-nitrophenoxy)pyrazine-2-carboxamide (14 mg) as a yellow oily substance.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. washthe organic phase was washed with water and saturated brine
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate:methanol:28% aqueous ammonia=95:4.5:0.5-90:9:1, chloroform: methanol=1:0-9:1)

Sources & evidence

ORD record
ord-9f97f43decde438cbfdc5f0334b59879
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09085540B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes