Tetrahydrofuran → 4-(5-(4-Chlorophenyl)-4-((dimethylamino) methyl)-2-propionylthiophen-3-yl)benzenesulfonamide

HRID 1053267Notes

Reaction equation

HRID 1053267 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)[C:9]=2[CH2:33][N:34]([CH3:36])[CH3:35])=[CH:4][CH:3]=1.[CH2:37]1COC[CH2:38]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13](=[O:14])[CH2:37][CH3:38])=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([NH2:26])(=[O:32])=[O:31])=[CH:21][CH:20]=3)[C:9]=2[CH2:33][N:34]([CH3:36])[CH3:35])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 867050275-(4-chlorophenyl)-4-((dimethylamino)methyl)-3-(4-(N-((dimethylamino) methylene)sulfamoyl)phenyl)-N-methoxy-N-methylthiophene-2-carboxamide2×

Product 1

HCID 601690864-(5-(4-Chlorophenyl)-4-((dimethylamino) methyl)-2-propionylthiophen-3-yl)benzenesulfonamideYield 19.28%

Conditions

Temperature
0 °C

Procedure

Grignard reagent (ethyl magnesium bromide, 0.48 g, 3.6 ml 1M solution in THF, 3.64 mmol) was added drop wise to a stirred solution of 5-(4-chlorophenyl)-4-((dimethylamino)methyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-N-methoxy-N-methylthiophene-2-carboxamide (compound 35e, 0.4 g, 0.72 mmol) in anhydrous THF (20 ml) at 25° C. The reaction mixture was then heated at 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 (15 ml). The mixture so formed was then extracted with ethyl acetate (2×30 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent from the dried organic layer was evaporated under reduced pressure to obtain a crude product, which was then purified by column chromatography over silica gel (100-200 mesh) using 60% ethyl acetate in hexanes as an eluent to obtain the title compound (0.065 g, 19.28%)

Workup

  1. temperatureThe reaction mixture was then heated at about 70 to about 75° C. for 2 hr
  2. customthe reaction mixture was quenched by addition of a saturated solution of ammonium chloride (15 ml)
  3. customThe mixture so formed
  4. extractionwas then extracted with ethyl acetate (2×30 ml)
  5. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  6. customThe solvent from the dried organic layer was evaporated 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-5a6323b2e2a94389893f90104e69a2b3
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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