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

HRID 82234

반응식

HRID 82234 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c9f39f745fd14be8be18f5ce3ebd860b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

연결된 노트

불러오는 중…