Methanol → 2-Chloro-N-{1-[2-(methylsulfonyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1178430노트

반응식

HRID 1178430 반응식
O[O:2][S:3]([O-:5])=O.[K+].[Cl:7][C:8]1[S:33][C:11]2[NH:12][C:13]([C:15]([NH:17][CH:18]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:28][CH2:29]SC)[C:19]3=[O:32])=[O:16])=[CH:14][C:10]=2[CH:9]=1.[CH3:34]O>O.CCOC(C)=O>[Cl:7][C:8]1[S:33][C:11]2[NH:12][C:13]([C:15]([NH:17][CH:18]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:28][CH2:29][S:3]([CH3:34])(=[O:5])=[O:2])[C:19]3=[O:32])=[O:16])=[CH:14][C:10]=2[CH:9]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 100477312-chloro-N-(1-[2-(methylthio)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6h-thieno[2,3-b]pyrrole-5-carboxamideHCID 23707502Potassium hydroxy sulfite

생성물 1

HCID 104339882-Chloro-N-{1-[2-(methylsulfonyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Oxone (701 mg, 1.14 mmol) in H2O (12 mL) was added to 2-chloro-N-{1-[2-(methylthio)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 34; 462 mg, 1.10 mmol) in MeOH (12 mL) and stirred for 18 hours. The mixture was diluted with EtOAc (100 mL) washed with saturated NaHCO3 (20 mL), dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography (DCM to DCM:THF (3:2) then DCM:MeOH (4:1)) to give 2 yellow solids. Each solid was triturated separately with refluxing Et2O (25 mL) and filtered, washed with Et2O (25 mL) then hexane (25 mL) to afford the title compounds (Example 35, 104 mg, 22% and Example 36, 230 mg, 46%) as solids.

후처리

  1. washwashed with saturated NaHCO3 (20 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography (DCM to DCM:THF (3:2)
  6. customDCM:MeOH (4:1)) to give 2 yellow solids
  7. customEach solid was triturated separately with refluxing Et2O (25 mL)
  8. filtrationfiltered
  9. washwashed with Et2O (25 mL)

출처 및 근거

ORD 기록
ord-79295d8d6c6045d985769682d7d96e94
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276517B2

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