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

HRID 1526167노트

반응식

HRID 1526167 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9f97f43decde438cbfdc5f0334b59879
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085540B2

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