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

HRID 1966825

반응식

HRID 1966825 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-303416e2845e487a912e17b70c68038f
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420666B2

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