HCID 86707933, compound → HCID 62705064, compound

HRID 714020Notes

Reaction equation

HRID 714020 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19](=[O:26])(=[O:25])[N:20]=CN(C)C)=[CH:15][CH:14]=3)[C:11]([CH3:27])=[C:10]([C:28](N(OC)C)=[O:29])[C:9]=2[CH3:34])=[CH:4][CH:3]=1.[CH2:35]([Mg]Br)[CH3:36]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH2:20])(=[O:26])=[O:25])=[CH:17][CH:18]=3)[C:11]([CH3:27])=[C:10]([C:28](=[O:29])[CH2:35][CH3:36])[C:9]=2[CH3:34])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 86707933HCID 86707933, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 62705064HCID 62705064, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-(4-Chlorophenyl)-1-(4-(N-((dimethylamino)methylene) sulfamoyl)phenyl)-N-methoxy-N,2,4-trimethyl-1H-pyrrole-3-carboxamide (step 3, 0.750 g, 1.49 mmol) in anhydrous THF (50 ml) at 0° C., ethyl magnesium bromide (Grignard reagent, 0.994 g, 7.4 ml, 7.46 mmol) was added dropwise and reaction mixture was heated to reflux for 1 h. The completion of reaction was monitored by TLC. After cooling, reaction mixture was quenched by addition of solution of saturated ammonium chloride (10 ml) and extracted with ethyl acetate (1×50 ml). Combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain a crude product; which was purified by column chromatography over silica gel (100-200 mesh) using 0.4% methanol in dichloromethane as an eluent to yield the title compound which was finally purified by preparative HPLC (0.062 g, 10%)

Workup

  1. customreaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 1 h
  4. customThe completion of reaction
  5. temperatureAfter cooling
  6. customreaction mixture
  7. customwas quenched by addition of solution of saturated ammonium chloride (10 ml)
  8. extractionextracted with ethyl acetate (1×50 ml)
  9. dry with materialCombined organic layer was dried over anhydrous Na2SO4
  10. customThe solvent was evaporated under reduced pressure
  11. customto obtain a crude product
  12. customwhich was purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-ef7e3f5e6e7d421e9552f1ce456e25a9
Source dataset
uspto-grants-2015_11
Patent number
US09187420B2

Reaction notes

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