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 1178430ノート

反応式

HRID 1178430 の反応式
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

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-79295d8d6c6045d985769682d7d96e94
出典データセット
uspto-grants-2007_10
特許番号
US07276517B2

反応ノート

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