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Sodium Bicarbonate → HCID 178448150, 화합물

HRID 539032
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HRID 539032 반응식
[CH:1]([C@@H:4]1[N:8]([C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[CH:16][C:17]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5[N:28]=[CH:27][N:26](COCC[Si](C)(C)C)[N:25]=5)=[CH:20][CH:19]=4)=[C:11]3[N:10]=2)[C:7](=[O:37])[NH:6][CH2:5]1)([CH3:3])[CH3:2].C([O-])(O)=O.[Na+]>CCO>[NH:26]1[CH:27]=[N:28][C:24]([C:21]2[CH:20]=[CH:19][C:18]([C:17]3[CH:16]=[N:15][N:12]4[CH:13]=[CH:14][C:9]([N:8]5[C@@H:4]([CH:1]([CH3:2])[CH3:3])[CH2:5][NH:6][C:7]5=[O:37])=[N:10][C:11]=34)=[CH:23][CH:22]=2)=[N:25]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

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HCID 516892Sodium BicarbonateHCID 67033259(S)-5-isopropyl-1-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one

생성물 1

HCID 178448150HCID 178448150, 화합물수율 67.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of (S)-5-isopropyl-1-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one (Example 25, Step 4, 12 mg, 0.023 mmol) and EtOH/6N aqueous HCl (1:2, 0.5 mL total) was heated at reflux for 3 hours. After cooling, the reaction mixture was neutralized by slow addition of saturated aqueous NaHCO3 solution. The mixture was extracted with dichloromethane, and the combined extracts were washed with brine, dried and concentrated. The residue was purified by column chromatography (12% MeOH in dichloromethane) to give (S)-1-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-5-isopropylimidazolidin-2-one (6 mg, 67%) as a pale yellow solid. LCMS (APCI+) m/z 389 [M+H]+.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. extractionThe mixture was extracted with dichloromethane
  5. washthe combined extracts were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (12% MeOH in dichloromethane)

출처 및 근거

ORD 기록
ord-ea3b1376814a4dee9ff25f0e48e418c2
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08865726B2

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