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Cesium carbonate → N-[6-Amino-5-(2,3-dichloro-5-methoxyphenyl)pyrazin-2-yl]-1-methyl-1H-pyrazole-5-carboxamide

HRID 2100344
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HRID 2100344 반응식
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)=[O:10])[CH:5]=[N:4][C:3]=1Cl.[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][C:22]([O:26][CH3:27])=[CH:21][C:20]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)=[O:10])[CH:5]=[N:4][C:3]=1[C:20]1[CH:21]=[C:22]([O:26][CH3:27])[CH:23]=[C:24]([Cl:25])[C:19]=1[Cl:18]
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 577991422-(2,3-Dichloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 57799151N-(6-Amino-5-chloropyrazin-2-yl)-1-methyl-1H-pyrazole-5-carboxamide

생성물 1

HCID 16661733N-[6-Amino-5-(2,3-dichloro-5-methoxyphenyl)pyrazin-2-yl]-1-methyl-1H-pyrazole-5-carboxamide수율 46.2%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

N-(6-Amino-5-chloropyrazin-2-yl)-1-methyl-1H-pyrazole-5-carboxamide (Preparation 2, 0.1 g, 0.396 mmol) was combined with 2,(2,3-dichloro-5-methoxy-phenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Preparation 18), (0.156 g, 0.515 mmol), cesium carbonate (0.129 g, 0.396 mmol) and palladium tetrakistriphenylphosphine (0.046 g, 0.04 mmol) and suspended in a mixture of 1,4-dioxane (1 ml) and water (0.5 ml). The reaction was heated at 80° C. for 5 hours. The reaction was allowed to cool to room temperature and then concentrated in vacuo. The residue was partitioned between aqueous sodium carbonate solution (20 ml) and ethyl acetate (20 ml) and the organic layer dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography, eluting with ethyl acetate:heptane 2:3 to 1:1, to afford the product as an off-white solid (72 mg).

후처리

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between aqueous sodium carbonate solution (20 ml) and ethyl acetate (20 ml)
  4. dry with materialthe organic layer dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate:heptane 2:3 to 1:1

출처 및 근거

ORD 기록
ord-77967d77034746c58e84c6a0fdda7bf8
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07572797B2

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