Water → 1-(4-methoxyphenyl)-3-(methylsulfonyl) 1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one

HRID 971136노트

반응식

HRID 971136 반응식
Cl[C:2]1[C:3](=[O:8])[NH:4][CH2:5][CH2:6][CH:7]=1.Cl/[C:10](=[N:15]\[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)/[S:11]([CH3:14])(=[O:13])=[O:12].CCN(CC)CC.O>C1(C)C=CC=CC=1.CCOC(C)=O.C(Cl)Cl>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([N:16]2[C:2]3[C:3](=[O:8])[NH:4][CH2:5][CH2:6][C:7]=3[C:10]([S:11]([CH3:14])(=[O:13])=[O:12])=[N:15]2)=[CH:22][CH:21]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 222404953-Chloro-5,6-dihydropyridin-2(1H)-oneHCID 22318579(1Z)-N-(4-Methoxyphenyl)-1-(methylsulfonyl)methanehydrazonoyl chloride

생성물 1

HCID 695158511-(4-methoxyphenyl)-3-(methylsulfonyl) 1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one수율 31.4%

시약·촉매·용매 3

HCID 1140Toluene용매2회HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매2회

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온도
85 °C

실험 절차

Part A. 3-Chloro-5,6-dihydro-2(1H)-pyridinone (10.0 g, 38.17 mmol) and (1Z)-1-[chloro(methylsulfonyl)methylene]-2-(4-methoxyphenyl)hydrazine (5.0 g, 38.17 mmol) were stirred in toluene (200 mL) at RT under N2. Et3N (30 mL, 215.24 mmol) in toluene (150 mL) was added dropwise to the solution. After addition, the mixture was heated at 85° C. overnight. After cooling, H2O was added. It was extracted with EtOAc (2×). The organic layers were washed with H2O (2×) and brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography (silica gel, CH2Cl2, then CH2Cl2:EtOAc=1:1, then EtOAc) to give 1-(4-methoxyphenyl)-3-(methylsulfonyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one (3.85 g, yield: 31%). LC/MS (ESI+) 322.4 (M+H)+, tR=1.79 min (10–90% CH3CN/H2O in a 4-min run).

후처리

  1. additionAfter addition
  2. temperatureAfter cooling
  3. extractionIt was extracted with EtOAc (2×)
  4. washThe organic layers were washed with H2O (2×) and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by flash column chromatography (silica gel, CH2Cl2

출처 및 근거

ORD 기록
ord-043fe4a4b0b84d588466a5d7a1ce95a0
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312214B2

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