Ethanol → N-(isobutoxycarbonyl)-2-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

HRID 361431

반응식

HRID 361431 반응식
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1)[CH2:8][CH3:9].Cl[C:20]1[C:25]([S:26]([N:29]([C:39]([O:41][CH2:42][CH:43]([CH3:45])[CH3:44])=[O:40])[C:30]2[C:35]([O:36][CH3:37])=[N:34][C:33]([CH3:38])=[CH:32][N:31]=2)(=[O:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=1.C(O)C>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH2:42]([O:41][C:39]([N:29]([C:30]1[C:35]([O:36][CH3:37])=[N:34][C:33]([CH3:38])=[CH:32][N:31]=1)[S:26]([C:25]1[C:20]([C:13]2[CH:14]=[CH:15][C:10]([CH2:7][CH2:8][CH3:9])=[CH:11][CH:12]=2)=[N:21][CH:22]=[CH:23][CH:24]=1)(=[O:28])=[O:27])=[O:40])[CH:43]([CH3:45])[CH3:44]

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 4100861(4-Propylphenyl)boronic acidHCID 11015197Isobutyl (2-chloropyridin-3-yl)sulfonyl(3-methoxy-5-methylpyrazin-2-yl)carbamate

생성물 1

HCID 21186267N-(isobutoxycarbonyl)-2-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide수율 76.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

Tetrakis(triphenylphosphine)palladium (0) (60 mg) was added to a deoxygenated solution of sodium carbonate (212 mg), 4-propylphenylboronic acid (328 mg) and 2-chloro-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (828 mg) in a mixture of water (5 ml), ethanol (8 ml) and toluene (16 ml). The mixture was stirred and heated under argon at 80° C. for 17 hours and then allowed to cool to ambient temperature. Ice water (25 g) was added and the reaction extracted with ethyl acetate (3×50 ml). The combined organic layers were dried (MgSO4) and evaporated to afford an amber oil. This was purified by chromatography on a silica gel Mega Bond Elut column, eluting with 20% ethyl acetate/isohexane to give N-(isobutoxycarbonyl)-2-(4-propylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (760 mg) as a solid, mass spectrum (+ve ESP): 499 (M+H)+.

후처리

  1. temperatureto cool to ambient temperature
  2. extractionthe reaction extracted with ethyl acetate (3×50 ml)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated
  5. customto afford an amber oil
  6. customThis was purified by chromatography on a silica gel Mega Bond Elut column
  7. washeluting with 20% ethyl acetate/isohexane

출처 및 근거

ORD 기록
ord-ba5fffec7fc54233900423251a233b0f
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866568

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