Chloroform → ethyl 5-(bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazole-5-carboxylate

HRID 1966825

Reaktionsgleichung

Reaktionsgleichung von HRID 1966825
[CH:1]1([NH:7][C:8]2[C:13]([CH:14]=[N:15][OH:16])=[CH:12][N:11]=[C:10]3[N:17]([CH2:20][CH3:21])[N:18]=[CH:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(Cl)Cl.[Br:26][CH2:27][C:28](=[CH2:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30].Cl[O-].[Na+]>ClCCl.O>[Br:26][CH2:27][C:28]1([C:29]([O:31][CH2:32][CH3:33])=[O:30])[O:16][N:15]=[C:14]([C:13]2[C:8]([NH:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:9]3[CH:19]=[N:18][N:17]([CH2:20][CH3:21])[C:10]3=[N:11][CH:12]=2)[CH2:34]1

Komponenten

7

Edukt 4

HCID 6212ChloroformHCID 3106202-(Bromomethyl)acrylic acid ethyl esterHCID 23665760Sodium HypochloriteHCID 866475994-cyclohexylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde oxime

Produkt 1

HCID 66732635ethyl 5-(bromomethyl)-3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydroisoxazole-5-carboxylateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(Cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde oxime (200 mg, 0.0006 mole) (example 8) was taken in dichloromethane: chloroform mixture (10 ml: 5 ml). Ethyl 2-(bromomethyl)acrylate (0.2 ml, 0.00103 mole) was added. Sodium hypochlorite (2.5 ml) was added drop wise. The reaction mixture was stirred overnight. Water was added, the mixture was extracted with chloroform, washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo. The crude compound obtained was purified by column chromatography.

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-303416e2845e487a912e17b70c68038f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420666B2

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