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

HRID 2308341Notes

Reaction equation

HRID 2308341 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-1a2f1594598944ccb907a06735f3907d
Source dataset
uspto-grants-2004_12
Patent number
US06835739B2

Reaction notes

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