Pyridine → N-{2-[N-(5-chloro(2-pyridyl))carbamoyl](3-thienyl)}(4-(2-sulfamoylphenyl)phenyl]carboxamide

HRID 2362796Notes

Reaction equation

HRID 2362796 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)(=[O:8])=[O:7])(C)(C)C.[NH2:24][C:25]1[CH:29]=[CH:28][S:27][C:26]=1[C:30]([NH:32][C:33]1[CH:38]=[C:37](Cl)[CH:36]=[CH:35][N:34]=1)=[O:31].N1C=CC=CC=1.[Cl:46]CCl>>[Cl:46][C:36]1[CH:37]=[CH:38][C:33]([NH:32][C:30]([C:26]2[S:27][CH:28]=[CH:29][C:25]=2[NH:24][C:19]([C:18]2[CH:17]=[CH:16][C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[S:6](=[O:7])(=[O:8])[NH2:5])=[CH:23][CH:22]=2)=[O:20])=[O:31])=[N:34][CH:35]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344Dichloromethane2×HCID 22596369HCID 22596369, compoundHCID 226016743-Amino-2-(4-chloro-2-pyridinyl)aminocarbonyl thiophene

Product 1

HCID 10229449N-{2-[N-(5-chloro(2-pyridyl))carbamoyl](3-thienyl)}(4-(2-sulfamoylphenyl)phenyl]carboxamide

Procedure

A solution of 4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)benzoyl chloride (1 equiv), 3-amino-2-(4-chloro-2-pyridinyl)aminocarbonyl thiophene (1 equiv), pyridine (5 equiv) in dichloromethane was stirred at rt overnight. The mixture was diluted with dichloromethane, washed with water, dried over Na2SO4, filtered and evaporated. The residue was refluxed with 1 mL of TFA for 2 h. After evaporation, reverse phase HPLC gave the title product. ES-MS 513 (M+1).

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. temperatureThe residue was refluxed with 1 mL of TFA for 2 h
  6. customAfter evaporation

Sources & evidence

ORD record
ord-89ab21df5bc249cfb5f0fabf9b0df70e
Source dataset
uspto-grants-2014_04
Patent number
US08691847B2

Reaction notes

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