Tetrahydrofuran → HCID 60169084, compound

HRID 1518704Notes

Reaction equation

HRID 1518704 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](N(OC)C)=[O:14])=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([S:25](=[O:32])(=[O:31])[N:26]=CN(C)C)=[CH:21][CH:20]=3)[CH:9]=2)=[CH:4][CH:3]=1.[CH2:33]1COC[CH2:34]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13](=[O:14])[CH2:33][CH3:34])=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([NH2:26])(=[O:31])=[O:32])=[CH:21][CH:20]=3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 86705028HCID 86705028, compound2×

Product 1

HCID 60169084HCID 60169084, compoundYield 14.6%

Conditions

Temperature
0 °C

Procedure

Grignard reagent (ethyl magnesium bromide, 0.67 g, 5.0 ml 1M solution in THF, 5.08 mmol) was added drop wise to a stirred solution of 5-(4-chlorophenyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-N-methoxy-N-methylthiophene-2-carboxamide (compound 33d, 0.5 g, 1.01 mmol) in anhydrous THF (15 ml) at 25° C. The reaction mixture was then heated to about 70 to about 75° C. for 2 hr. The progress of the reaction was monitored by TLC. After cooling the reaction mixture to 0° C., the reaction mixture was quenched by addition of a saturated solution of ammonium chloride (10 ml). The mixture so obtained was extracted with ethyl acetate (2×30 ml). the combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain a crude product, which was then purified by column chromatography over silica gel (100-200 mesh) using 40% ethyl acetate in hexanes as an eluent to obtain the title compound (0.06 g, 14.6%).

Workup

  1. temperatureThe reaction mixture was then heated to about 70 to about 75° C. for 2 hr
  2. customthe reaction mixture was quenched by addition of a saturated solution of ammonium chloride (10 ml)
  3. customThe mixture so obtained
  4. extractionwas extracted with ethyl acetate (2×30 ml)
  5. dry with materialthe combined organic layer was dried over anhydrous Na2SO4
  6. customThe solvent was evaporated from the dried organic layer under reduced pressure
  7. customto obtain a crude product, which
  8. customwas then purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-71793eecb81d4070a4b4494706d16682
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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