Methanol → N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-1,3-dihydro-2-benzofuran-5-yl)acetyl]thiophene-3-sulfonamide

HRID 2047256Notes

Reaction equation

HRID 2047256 reaction equation
[Cl:1][C:2]1[C:3]([CH3:33])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16]1([CH2:22][C:23]2[C:31]([CH3:32])=[CH:30][C:26]3[CH2:27][O:28][CH2:29][C:25]=3[CH:24]=2)SCCCS1)(=[O:10])=[O:9].CO.O.[O:37]1CCCC1>[Cl-].[Na+].O.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[C:3]([CH3:33])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16](=[O:37])[CH2:22][C:23]1[C:31]([CH3:32])=[CH:30][C:26]2[CH2:27][O:28][CH2:29][C:25]=2[CH:24]=1)(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8028TetrahydrofuranHCID 86691252N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-{2-[(6-methyl-1,3-dihydro-2-benzofuran-5-yl)methyl]-1,3-dithian-2-yl}thiophene-3-sulfonamide

Product 1

HCID 71654814N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-1,3-dihydro-2-benzofuran-5-yl)acetyl]thiophene-3-sulfonamideYield 18%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-{2-[(6-methyl-1,3-dihydro-2-benzofuran-5-yl)methyl]-1,3-dithian-2-yl}thiophene-3-sulfonamide described in Production Example 1-7 (300 mg, 0.55 mmol), methanol (20 mL), water (2 mL) and silver nitrate (940 mg, 5.5 mmol) was stirred for 3 days at 55° C. The reaction mixture was allowed to cool to room temperature, tetrahydrofuran (40 mL) and brine (1 mL) were added at that temperature, and the mixture was filtered with Celite. The filtrate was extracted by addition of ethyl acetate (200 mL), water (100 mL) and saturated aqueous citric acid solution (1 mL). The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:9), and then further purified by silica gel thin-layer chromatography (methanol:ethyl acetate=1:32) to give the title compound (45 mg, 18% yield).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe mixture was filtered with Celite
  3. extractionThe filtrate was extracted by addition of ethyl acetate (200 mL), water (100 mL) and saturated aqueous citric acid solution (1 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:9)
  8. customfurther purified by silica gel thin-layer chromatography (methanol:ethyl acetate=1:32)

Sources & evidence

ORD record
ord-813d2139ab4d448c9f8690e911711a69
Source dataset
uspto-grants-2013_11
Patent number
US08592470B2

Reaction notes

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