Methanol → N-(4-Benzoylpyrrolidino)-1-(4-methoxyphenyl)-3-(methylsulfonyl)-1H-pyrazole-5-carboxamide

HRID 610132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 610132
[C:1]([CH:9]1[CH2:13][N:12]([NH:14][C:15]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:20]=[C:19](SC)[CH:18]=2)=[O:16])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[O:33][S:34]([O-:36])=O.[K+].[CH3:38]O>O>[C:1]([CH:9]1[CH2:13][N:12]([NH:14][C:15]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:20]=[C:19]([S:34]([CH3:38])(=[O:36])=[O:33])[CH:18]=2)=[O:16])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 10238249N-(4-benzoylpyrrolidino)-1-(4-methoxyphenyl)-3-(methylthio)-1H-pyrazole-5-carboxamideHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 10174009N-(4-Benzoylpyrrolidino)-1-(4-methoxyphenyl)-3-(methylsulfonyl)-1H-pyrazole-5-carboxamideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

N-(4-benzoylpyrrolidino)-1-(4-methoxyphenyl)-3-(methylthio)-1H-pyrazole-5-carboxamide (200 mg, 0.46 mmol) was dissolved in MeOH (6 mL). A solution of Oxone (561 mg, 0.91 mmol) in H2O (3 mL) was added, and the resulting mixture stirred at room temperature under Ar for 17 hours. The reaction was diluted with H2O and extracted twice with CHCl3. The combined organic extracts were dried over Na2SO4, filtered, and evaporated. The crude product was purified by preparative HPLC on a C-18 reversed-phase column (10-70% MeCN/H2O/0.05% TFA) to yield a white powder (200 mg, 93%). 1H NMR (CDCl3): δ8.98 (s, 1H), 7.52 (s, 1H), 7.39 (m, 6H), 6.95 (d, 2H, J=8.8), 3.84 (s, 3H), 3.65 (t, 2H, J=6.6 ), 3.41 (t, 2H, J=6.2 ), 3.28 (s, 3H), 1.93 (m, 4H).

Aufarbeitung

  1. extractionextracted twice with CHCl3
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by preparative HPLC on a C-18 reversed-phase column (10-70% MeCN/H2O/0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-841c353190e24ac1b312e7f6902dad76
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998424

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