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

HRID 1966825

反応式

HRID 1966825 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-303416e2845e487a912e17b70c68038f
出典データセット
uspto-grants-2013_04
特許番号
US08420666B2

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