Hydrochloric Acid → 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone

HRID 1969884노트

반응식

HRID 1969884 반응식
[CH2:1]([CH:3]1[CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH:4]1[C:12]1[N:16]2[C:17]3[CH:23]=[CH:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:18]=3[N:19]=[CH:20][C:15]2=[N:14][N:13]=1)[CH3:2].Cl>C1COCC1>[CH2:1]([CH:3]1[CH:4]([C:12]2[N:16]3[C:17]4[CH:23]=[CH:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[C:18]=4[N:19]=[CH:20][C:15]3=[N:14][N:13]=2)[CH2:5][C:6](=[O:7])[CH2:11]1)[CH3:2]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 585574851-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

생성물 1

HCID 585572963-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone수율 81.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (3.87 g, 8.72 mmol) in THF (30 mL), was added aqueous HCl (1N, 26.2 mL) at about 0° C. The ice bath was removed and the reaction was stirred at ambient temperature for about 6 h. THF was removed under reduced pressure. The aqueous phase was neutralized by the addition of saturated aqueous NaHCO3 and was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (60 mL), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel column chromatography using 20 to 80% EtOAc in DCM to yield 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone (2.84 g, 81%) as a yellow amorphous solid. LC/MS (Table 1, Method a) Rt=2.44 min; MS m/z: 400 (M+H)+.

후처리

  1. customThe ice bath was removed
  2. customTHF was removed under reduced pressure
  3. additionThe aqueous phase was neutralized by the addition of saturated aqueous NaHCO3
  4. extractionwas extracted with EtOAc (2×50 mL)
  5. washThe combined organic extracts were washed with brine (60 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-4a49cdf378c8478bb651d2d21e6fd9fa
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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