Water → HCID 12115053, compound

HRID 1830840Notes

Reaction equation

HRID 1830840 reaction equation
[N:1]1([CH2:10][C:11]2[N:16]=[C:15]3[S:17][C:18]4[CH2:23][S:22][CH2:21][CH2:20][C:19]=4[C:14]3=[C:13]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:12]=2[Cl:32])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.ClC1C=CC=C(C(OO)=[O:41])C=1.O>C(Cl)Cl>[N:1]1([CH2:10][C:11]2[N:16]=[C:15]3[S:17][C:18]4[CH2:23][S:22](=[O:41])[CH2:21][CH2:20][C:19]=4[C:14]3=[C:13]([C:24]3[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=3)[C:12]=2[Cl:32])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 22048208HCID 22048208, compound

Product 1

HCID 12115053HCID 12115053, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound obtained in Example 1 (800 mg) in methylene chloride (20 ml) was added m-chloroperbenzoic acid (70%, 400 mg) under ice cooling and then the resulting mixture was stirred at the same temperature for 1 hour. The reaction mixture was poured into water and extracted with methylene chloride. The methylene chloride layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and water, dried (MgSO4), and then evaporated under reduced pressure to remove the solvent. The residue was subjected to column chromatography on silica gel to obtain 2-[(1H-benzimidazol-1-yl)methyl]-3-chloro-4-(4-methoxyphenyl)-7-oxido-5,8-dihydro-6H-thiopyrano[4′,3′:4,5]thieno[2,3-b]pyridine (530 mg, 64%) from the eluates with ethyl acetate-methanol (20:1). It was recrystallized from THF-hexane. Colorless prisms. Melting point 233–235° C.

Workup

  1. extractionextracted with methylene chloride
  2. washThe methylene chloride layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and water
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-4461bd2fb260408db649c6df2feb855b
Source dataset
uspto-grants-2006_06
Patent number
US07067527B2

Reaction notes

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