Tetrahydrofuran → HCID 60168906, compound

HRID 1518686Notes

Reaction equation

HRID 1518686 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]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[S:17][C:16]=2[C:27](N(OC)C)=[O:28])=[CH:11][CH:10]=1)(=[O:8])=[O:7])C.[CH2:33]1COC[CH2:34]1>>[CH3:20][C:19]1[C:15]([C:12]2[CH:13]=[CH:14][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:10][CH:11]=2)=[C:16]([C:27](=[O:28])[CH2:33][CH3:34])[S:17][C:18]=1[N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 86705024HCID 86705024, compound2×

Product 1

HCID 60168906HCID 60168906, compound

Conditions

Temperature
72.5 °C

Procedure

To a stirred solution of 3-(4-(N-((dimethylamino)methylene) sulfamoyl)phenyl)-N-methoxy-N,4-dimethyl-5-morpholinothiophene-2-carboxamide (compound 24f, 0.120 g, 0.25 mmol) in anhydrous THF (10 ml) at 25° C., Grignard reagent (ethyl magnesium bromide, 0.17 g, 1.25 ml, 1.25 mmol) was added dropwise and the reaction mixture was heated to 70-75° C. for 1 hr. The progress of the reaction was monitored by TLC. After cooling the reaction mixture to 0° C., reaction mixture was quenched by adding a saturated ammonium chloride solution (10 ml) and the resulting mixture was extracted with ethyl acetate (2×20 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent in the dried organic layer was evaporated under a reduced pressure to obtain a crude product, which was purified by column chromatography over silica gel (100-200 mesh) using 40-45% ethyl acetate in hexane as an eluent to obtain the title compound which was further purified by precipitation by dissolving 0.056 g of this compound in ethyl acetate (1.0 ml) and precipitating it by the slow addition of diisopropyl ether. The precipitate was filtered to obtain the title compound. (0.047 g, 48%).

Workup

  1. temperatureAfter cooling the reaction mixture to 0° C.
  2. customreaction mixture
  3. customwas quenched
  4. additionby adding a saturated ammonium chloride solution (10 ml)
  5. extractionthe resulting mixture was extracted with ethyl acetate (2×20 ml)
  6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  7. customThe solvent in the dried organic layer was evaporated under a reduced pressure
  8. customto obtain a crude product, which
  9. customwas purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-41d3f93e2b374f28a706def75df6e5b5
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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