Hydroxyamine hydrochloride → (S)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-ylamino)cyclohexanone oxime

HRID 527037ノート

反応式

HRID 527037 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][C:20](=O)[CH2:19]4)[C:14]([F:25])=[CH:13][N:12]=3)=[CH:9][N:8]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:5]2=[N:6][CH:7]=1.Cl.[NH2:37][OH:38]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][C:20](=[N:37][OH:38])[CH2:19]4)[C:14]([F:25])=[CH:13][N:12]=3)=[CH:9][N:8]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:5]2=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 443297Hydroxyamine hydrochlorideHCID 67286479(3S)-3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]cyclohexanone

生成物 1

HCID 86719749(S)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-ylamino)cyclohexanone oxime

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To solution of (3S)-3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]cyclohexanone (0.41 g, 0.81 mmol) in EtOH (8.2 mL) was added hydroxylamine hydrochloride (0.11 g, 1.61 mmol). The reaction mixture was stirred at room temperature overnight. Then the mixture was warmed to 70° C. for 15 min. The reaction mixture was concentrated in vacuo, suspended in EtOAc-DCM, washed with half saturated brine (2×) and filtered through a SiO2 plug. The resulting residue was azeotroped with CH3CN (2×) to provide an off white powder which was used without further purification.

後処理

  1. temperatureThen the mixture was warmed to 70° C. for 15 min
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. washwashed with half saturated brine (2×)
  4. filtrationfiltered through a SiO2 plug
  5. customThe resulting residue was azeotroped with CH3CN (2×)
  6. customto provide an off white powder which
  7. customwas used without further purification

出典と根拠

ORDレコード
ord-ef01249bc8c449cea654af3b85bbe622
出典データセット
uspto-grants-2016_05
特許番号
US09345708B2

反応ノート

読み込み中…