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Tetrabutylammonium Fluoride → 2-(5-hydroxymethyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

HRID 246341
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HRID 246341 반응식
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26](C)(C)[O:27][SiH2]C(C)(C)C)[CH:24]=4)[N:19]([CH3:35])[N:18]=3)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([CH2:26][OH:27])[CH:24]=4)[N:19]([CH3:35])[N:18]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 131731223N-tert-butyl-2-[5-(2-tert-butylsilyloxypropan-2-yl)-1-methylindazol-3-yl]-5-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyrazine-7-carboxamide

생성물 1

HCID 712794532-(5-hydroxymethyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide수율 47%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (106 mg, 0.17 mmol) in THF (2 mL) was added tetrabutylammonium fluoride (1.0 M in THF, 1.7 mL, 1.7 mmol). The reaction mixture was stirred at room temperature for 10 min then heated at reflux for 2 h. After cooling to room temperature, the reaction was quenched with water and extracted with EtOAc and then with 5% MeOH/CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated. The residue was triturated with EtOAc/MeOH and the solids collected via filtration to afford 30 mg (47%) of 2-(5-hydroxymethyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a light yellow solid.

후처리

  1. temperaturethen heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling to room temperature
  4. customthe reaction was quenched with water
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was triturated with EtOAc/MeOH
  9. filtrationthe solids collected via filtration

출처 및 근거

ORD 기록
ord-c63e7028e711420e80550f070b501587
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658646B2

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