Pyridine → (2R)-N-[2-Chloro-4-[(2-sulfamoylphenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methyl-propanamide

HRID 2283309Notes

Reaction equation

HRID 2283309 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:18](Cl)(=[O:20])=[O:19])[CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:17])[C@:10]([OH:16])([CH3:15])[C:11]([F:14])([F:13])[F:12].N1C=CC=CC=1.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35]([NH2:38])(=[O:37])=[O:36].CCCC(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:18](=[O:20])(=[O:19])[NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[S:35](=[O:37])(=[O:36])[NH2:38])[CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:17])[C@:10]([OH:16])([CH3:15])[C:11]([F:14])([F:13])[F:12]

Participants

8

Reactant 4

HCID 1049PyridineHCID 78922-MethylpentaneHCID 728942-AminobenzenesulfonamideHCID 545344943-chloro-4-[[(2R)-3,3,3-trifluoro-2-hydroxy-2-methyl-propanoyl]amino]benzenesulfonyl chloride

Product 1

HCID 57750920(2R)-N-[2-Chloro-4-[(2-sulfamoylphenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methyl-propanamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-chloro-4-[[(2R)-3,3,3-trifluoro-2-hydroxy-2-methyl-propanoyl]amino]benzenesulfonyl chloride (110 mg, 0.3 mmol) in DCM (5 ml) and pyridine (30 μl, 0.33 mmol) was added DMAP (˜2 mg) followed by 2-aminobenzenesulfonamide (52 mg, 0.3 mmol). The resulting mixture was stirred at RT for 18 h. The solution was concentrated and partitioned between ethyl acetate (6 ml) and 1M HCl (5 ml). The organic layer was separated, washed with saturated NaHCO3, dried (MgSO4) and evaporated to give a gum which was dissolved in a small amount of ethyl acetate and then iso-hexane was added to precipitate the title compound as a solid. LCMS 502.2 (M+H), Rf 7.64 min. [Column: HYPERSIL ODS; Flow Rate: 1.5 ml/min; Detector Wavelength: 254 nm; Solvent A: 0.1% Formic Acid in Water; Solvent B: 0.1% Formic Acid in Acetonitrile; Gradient: 5-95% B]

Workup

  1. concentrationThe solution was concentrated
  2. custompartitioned between ethyl acetate (6 ml) and 1M HCl (5 ml)
  3. customThe organic layer was separated
  4. washwashed with saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a gum which
  8. customto precipitate the title compound as a solid

Sources & evidence

ORD record
ord-29fe6cce298c405b9bc0755be33a7c60
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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