Ethanol → HCID 58382138, 화합물

HRID 1628020노트

반응식

HRID 1628020 반응식
[CH:1]1([NH:7][C:8]2[C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][N:11]=[C:10]3[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:21][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].CCO>O1CCOCC1>[CH:1]1([NH:7][C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[C:10]3[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:21][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 583819901H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-(cyclohexylamino)-1-[[2-(trimethylsilyl)ethoxy]methyl]-, ethyl ester

생성물 1

HCID 58382138HCID 58382138, 화합물수율 99%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To the suspension of ethyl 4-(cyclohexylamino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.77 g, 1.9 mmol) in 1,4-dioxane (12 mL) was added aquoeous NaOH (1 N, 12 mL, 12 mmol). The mixture was stirred at rt for about 48 h. To the mixture was added EtOH (1 mL) and the mixture was heated at about 50° C. for about 24 h. The mixture was concentrated under reduced pressure and aqueous HCl (0.5 M, 10 mL) was added and the mixture extracted with EtOAc (25 mL). The solid in the organic layer was collected by vacuum filtration. The filtrate and aqueous layer were recombined and separated. The solid was dissolved in EtOAc (˜150 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo and dried under reduced pressure at about rt to give 4-(cyclohexylamino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.713 g, 99%): LC/MS (Table 2, Method b) Rt=2.74 min.; MS m/z: 390 (M+H)+.

후처리

  1. temperaturethe mixture was heated at about 50° C. for about 24 h
  2. concentrationThe mixture was concentrated under reduced pressure and aqueous HCl (0.5 M, 10 mL)
  3. additionwas added
  4. extractionthe mixture extracted with EtOAc (25 mL)
  5. filtrationThe solid in the organic layer was collected by vacuum filtration
  6. customseparated
  7. dissolutionThe solid was dissolved in EtOAc (˜150 mL)
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customdried under reduced pressure at about rt

출처 및 근거

ORD 기록
ord-07e280b002a74fb1862246876491f8fc
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785639B2

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