Potassium Carbonate → 2-[3-(3-chloro-5-cyano-phenoxy)-2-oxo-4-(trifluoromethyl)-1-pyridyl]-N-(2-chloro-4-sulfamoyl-phenyl)acetamide

HRID 1952363Notes

Reaction equation

HRID 1952363 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:12](=[O:21])[NH:13][CH:14]=[CH:15][C:16]=2[C:17]([F:20])([F:19])[F:18])[CH:9]=1)[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].[NH2:28][S:29]([C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:42])[CH2:40]Br)=[C:34]([Cl:43])[CH:33]=1)(=[O:31])=[O:30]>CN(C)C=O.C(OCC)(=O)C>[NH2:28][S:29]([C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:42])[CH2:40][N:13]2[CH:14]=[CH:15][C:16]([C:17]([F:18])([F:19])[F:20])=[C:11]([O:10][C:8]3[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([Cl:1])[CH:9]=3)[C:12]2=[O:21])=[C:34]([Cl:43])[CH:33]=1)(=[O:31])=[O:30]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 584600483-Chloro-5-((1,2-dihydro-2-oxo-4-(trifluoromethyl)-3-pyridinyl)oxy)benzonitrileHCID 59511722N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoAcetamide

Product 1

HCID 426448762-[3-(3-chloro-5-cyano-phenoxy)-2-oxo-4-(trifluoromethyl)-1-pyridyl]-N-(2-chloro-4-sulfamoyl-phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 3-chloro-5-{[2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile (3C, 0.050 g, 0.159 mmol) and potassium carbonate (0.022 g, 0.159 mmol) suspended in dimethylformamide (1 mL) was added N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoacetamide (0.052 g, 0.149 mmol) as a solution in dimethylformamide (1 mL). The reaction mixture was allowed to stir at room temperature. After 16 hours, the reaction mixture was diluted with ethyl acetate (20 mL), washed with water (3×10 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on a pre-packed silica gel Redi Sep 12 gram column, eluting with 0-5% methanol in CH2Cl2 to yield the title compound. 1H NMR (DMSO-d6) δ 10.23 (s, 1H), 8.05-7.96 (m, 2H), 7.89 (d, J=2.1 Hz, 1H), 7.76-7.72 (m, 2H), 7.55-7.53 (m, 1H), 7.52-7.50 (m, 1H), 7.45 (s, 2H), 6.68 (d, 0.1=7.1 Hz, 1H), 5.02 (s, 2H). HRMS (M+1)=560.998.

Workup

  1. washwashed with water (3×10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on a pre-packed silica gel Redi Sep 12 gram column
  6. washeluting with 0-5% methanol in CH2Cl2

Sources & evidence

ORD record
ord-a9a170dd6a784beb99fdee04b99cc2ac
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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