Tetrahydrofuran → 4-(5-(4-Methoxyphenyl)-4-methyl-2-propionylthiophen-3-yl) benzene sulfonamide

HRID 1053260Notes

Reaction equation

HRID 1053260 reaction equation
CN(C=[N:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([CH3:20])=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[S:17][C:16]=2[C:29](N(OC)C)=[O:30])=[CH:11][CH:10]=1)(=[O:8])=[O:7])C.[CH2:35]1COC[CH2:36]1>>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([C:18]2[S:17][C:16]([C:29](=[O:30])[CH2:35][CH3:36])=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:10][CH:11]=3)[C:19]=2[CH3:20])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 867050253-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-N-methoxy-5-(4-methoxyphenyl)-N,4-dimethylthiophene-2-carboxamide2×

Product 1

HCID 601687004-(5-(4-Methoxyphenyl)-4-methyl-2-propionylthiophen-3-yl) benzene sulfonamideYield 37%

Conditions

Temperature
0 °C

Procedure

Grignard reagent (ethyl magnesium bromide, 3.59 g, 26.8 ml, 26.94 mmol) was added drop wise to a stirred solution of 3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-N-methoxy-5-(4-methoxyphenyl)-N,4-dimethylthiophene-2-carboxamide (compound 7f, 2.7 g, 5.8 mmol) in anhydrous THF (100 ml) at 25° C., and the reaction mixture was heated at about 70 to about 75° C. for 1 hr. The progress of the reaction was monitored by TLC. After cooling the reaction mixture to 0° C., the reaction mixture was quenched by adding a solution of saturated ammonium chloride (50 ml) and the resulting mixture was extracted with ethyl acetate (2×100 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 purified by Preparative HPLC to obtain the title compound (0.84 g, 37%).

Workup

  1. temperaturethe reaction mixture was heated at about 70 to about 75° C. for 1 hr
  2. customthe reaction mixture was quenched
  3. additionby adding a solution of saturated ammonium chloride (50 ml)
  4. extractionthe resulting mixture was extracted with ethyl acetate (2×100 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
  8. customwhich was purified by Preparative HPLC

Sources & evidence

ORD record
ord-f8968903f72b4411933265ff872d935d
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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