Dimethyl Sulfoxide → HCID 86711870, compound

HRID 623784Notes

Reaction equation

HRID 623784 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]([F:16])([F:15])[F:14])=[C:11](Br)[C:10]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:9]1[C:25]([N:27]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:28])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][S:35]([O-:37])=[O:36].[Na+].CS(C)=O.CNCCNC>ClCCl.O>[CH2:1]([N:8]1[C:12]([C:13]([F:16])([F:15])[F:14])=[C:11]([S:35]([CH3:34])(=[O:37])=[O:36])[C:10]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:9]1[C:25]([N:27]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:28])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 86711855HCID 86711855, compound

Product 1

HCID 86711870HCID 86711870, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

1-Benzyl-4-bromo-3-(4-chlorophenyl)-N-(2,2-dimethylpropyl)-N-methyl-5-(trifluoromethyl)pyrrole-2-carboxamide (100 mg, 0.18 mmol) followed by SODIUM METHANESULFINATE (4.0 equiv., 0.078 g, 0.74 mmol), COPPER(I) TRIFLATE BENZENE COMPLEX (0.1 equiv., 0.010 g, 0.018 mmol), DIMETHYL SULFOXIDE (0.6 mL) and N,N′-DIMETHYLETHYLENEDIAMINE (0.2 equiv., 0.003 g, 0.037 mmol) added to reactivial. Flushed with Nitrogen and heated at 140° C. for 18 hours (overnight). Black solid residue formed. Work Up: Diluted with 50 ml Dichloromethane and 100 ml Water then filtered to remove solids. Dichloromethane/Water shaken and separated. Aqueous extracted 2×50 ml Dichloromethane. Organics combined and filtered through hydrophobic frit, then reduced under vacuum. Purification: Purified via Preparative HPLC over 2 injections using 50-95% acetonitrile/water (0.1% Formic Acid) over 15 minutes collecting at 254 nm. Pure fractions combined and reduced under vacuum to yield product as 51.4 mg (0.09 mmol) beige solid.

Workup

  1. additionadded to reactivial
  2. customFlushed with Nitrogen
  3. customBlack solid residue formed
  4. filtrationthen filtered
  5. customto remove solids
  6. customseparated
  7. extractionAqueous extracted 2×50 ml Dichloromethane
  8. filtrationfiltered through hydrophobic frit
  9. customPurification
  10. customPurified via Preparative HPLC over 2 injections
  11. customover 15 minutes
  12. customcollecting at 254 nm

Sources & evidence

ORD record
ord-31d16f49db8a4942a47934bf44697c00
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

Loading…