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Trifluoroacetic acid → HCID 178446249, 화합물

HRID 1920854
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HRID 1920854 반응식
[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[C:13]([C:17]([CH3:29])([CH2:27][CH3:28])[CH2:18][NH:19]C(=O)OC(C)(C)C)[CH:14]=[CH:15][CH:16]=2)[NH:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[C:13]([C:17]([CH3:29])([CH2:27][CH3:28])[CH2:18][NH2:19])[CH:14]=[CH:15][CH:16]=2)[NH:4][N:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 178446750HCID 178446750, 화합물

생성물 1

HCID 178446249HCID 178446249, 화합물수율 55.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

tert-butyl 2-(3-(3-chloro-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylbutylcarbamate (60 mg, 0.1446 mmol) was dissolved in dry DCM (2 mL) and cooled in an ice-bath. TFA (2 mL,) was added slowly dropwise and the resultant was stirred at 0° C. for ˜25 minutes and at RT for ˜45 minutes. The reaction mixture was concentrated under reduced pressure and partitioned between EtOAc and saturated Na2CO3. The aqueous layer was extracted with EtOAc (3×10 mL) and the combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a slightly yellow gum. The resulting mixture was purified by column chromatography (9% MeOH/1% NH4OH in DCM, ˜50 mL silica) to give a white solid (25.2 mg, 55% Yield).

후처리

  1. temperaturecooled in an ice-bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompartitioned between EtOAc and saturated Na2CO3
  4. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a slightly yellow gum
  9. customThe resulting mixture was purified by column chromatography (9% MeOH/1% NH4OH in DCM, ˜50 mL silica)

출처 및 근거

ORD 기록
ord-94ef812a24004f4d8b55053d7c579243
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08173635B2

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