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

HRID 558106Notes

Reaction equation

HRID 558106 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-0346ac1ea706471ea12235dd9952bdb1
Source dataset
uspto-grants-2011_11
Patent number
US08063036B2

Reaction notes

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