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

HRID 971136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971136
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

Komponenten

8

Edukt 4

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

Produkt 1

HCID 695158511-(4-methoxyphenyl)-3-(methylsulfonyl) 1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-oneAusbeute 31,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-043fe4a4b0b84d588466a5d7a1ce95a0
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312214B2

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