Hydrochloric Acid → N-tert-butyl-2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylbenzenesulfonamide

HRID 229598Notes

Reaction equation

HRID 229598 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:12]=[CH:11][C:10]=1[CH2:18][CH2:19][NH:20][S:21]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:27]([NH2:29])=O)(=[O:23])=[O:22])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.Cl>ClCCl.O>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([CH:15]([CH3:16])[CH3:17])[CH:12]=[CH:11][C:10]=1[CH2:18][CH2:19][NH:20][S:21]([C:24]1[CH:25]=[C:26]([C:27]#[N:29])[CH:30]=[CH:31][C:32]=1[O:33][CH3:34])(=[O:23])=[O:22])(=[O:8])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 9845Trifluoroacetic anhydrideHCID 184569453-[[2-(2-Tert-butylsulfamoyl-4-isopropylphenyl)ethyl]sulfamoyl]-4-methoxybenzamide

Product 1

HCID 17856311N-tert-butyl-2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylbenzenesulfonamideYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 420 mg of 3-[[2-(2-tert-butylsulfamoyl-4-isopropylphenyl)ethyl]sulfamoyl]-4-methoxybenzamide in 30 mL of dichloromethane were added 0.48 mL of triethylamine and 0.245 mg of trifluoroacetic anhydride under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction mixture was added 1 mL of triethylamine, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture were added water and 30 mL of 1 mol/L hydrochloric acid, and the mixture was extracted three times with 30 mL of dichloromethane. The organic layers were combined, washed with water, and brine, and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, ethyl acetate and hexane were added to the residue, and the crystal was collected by filtration to give 325 mg of N-tert-butyl-2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylbenzenesulfonamide.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 2 hours
  3. extractionthe mixture was extracted three times with 30 mL of dichloromethane
  4. washwashed with water, and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter the solvent was removed under reduced pressure, ethyl acetate and hexane
  7. additionwere added to the residue
  8. filtrationthe crystal was collected by filtration

Sources & evidence

ORD record
ord-a1c90a9d75fa41f48317af9e00e8f0bf
Source dataset
uspto-grants-2009_07
Patent number
US07563822B2

Reaction notes

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