Water → 2-(3-formylphenyl)-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide

HRID 82234

反応式

HRID 82234 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][C:25]1[CH:26]=[C:27]([CH2:31][C:32]([NH:34][C:35]2[CH:36]=[N:37][CH:38]=[C:39]([C:41]([C:43]3[C:51]4[CH:50]=[N:49][CH:48]=[N:47][C:46]=4[N:45]([CH:52]([CH3:54])[CH3:53])[CH:44]=3)=[O:42])[CH:40]=2)=[O:33])[CH:28]=[CH:29][CH:30]=1.O>ClCCl>[CH:24]([C:25]1[CH:26]=[C:27]([CH2:31][C:32]([NH:34][C:35]2[CH:36]=[N:37][CH:38]=[C:39]([C:41]([C:43]3[C:51]4[CH:50]=[N:49][CH:48]=[N:47][C:46]=4[N:45]([CH:52]([CH3:54])[CH3:53])[CH:44]=3)=[O:42])[CH:40]=2)=[O:33])[CH:28]=[CH:29][CH:30]=1)=[O:23]

参加物

5

反応物 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 708177872-[3-(hydroxymethyl)phenyl]-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide

生成物 1

HCID 866720722-(3-formylphenyl)-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Dess Martin Periodinane (392 mg, 0.93 mmol) was added to a solution of (2-[3-(hydroxymethyl)phenyl]-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide (Preparation 193, 265 mg, 0.62 mmol) in dichloromethane (15 mL) and the mixture was stirred at room temperature for 18 hours. Water (10 mL) was added and the aqueous layer extracted with a 95:5 mixture of dichloromethane/methanol (3×10 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography using silica gel (gradient of dichloromethane to dichloromethane/methanol (10:1 to 9:1) to afford the title compound as a brown solid in 80% yield, 211 mg.

後処理

  1. extractionthe aqueous layer extracted with a 95:5 mixture of dichloromethane/methanol (3×10 mL)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-c9f39f745fd14be8be18f5ce3ebd860b
出典データセット
uspto-grants-2014_09
特許番号
US08846698B2

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