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 1247513Notes

Reaction equation

HRID 1247513 reaction equation
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

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7b428b5002404adc80a9c7aebdca0ac0
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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