Sodium ethanethiolate → 4-(2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-ol

HRID 8267

Reaktionsgleichung

Reaktionsgleichung von HRID 8267
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:13]3[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[N:16][N:15]4[CH2:24][CH2:25][CH2:26][C:14]=34)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C([S-])C.[Na+]>CN(C)C=O>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]1[C:13]([C:7]2[C:6]3[C:11](=[CH:12][C:3]([OH:2])=[CH:4][CH:5]=3)[N:10]=[CH:9][CH:8]=2)=[C:14]2[CH2:26][CH2:25][CH2:24][N:15]2[N:16]=1

Komponenten

4

Edukt 2

HCID 4459711Sodium ethanethiolateHCID 219925657-Methoxy-4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline

Produkt 1

HCID 1355066154-(2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 7-methoxy-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (53 mg, 0.16 mmol) in N,N-dimethylformamide (3 mL) at room temperature is added sodium ethanthiolate (133 mg, 1.6 mmol). The solution is refluxed for 4 h, cooled, and concentrated in vacuo. The residue is dissolved in methanol and loaded onto an SCX column. The column is washed with water, methanol, and 7 N ammonia in methanol. The appropriate fraction is concentrated in vacuo to yield the title compound, 28 mg (56%), as a yellow solid.

Aufarbeitung

  1. temperatureThe solution is refluxed for 4 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in methanol
  5. washThe column is washed with water, methanol, and 7 N ammonia in methanol
  6. concentrationThe appropriate fraction is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cf9a8429bbc34b0c827d1a9299d8cfdd
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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