Potassium Carbonate → 2-[5-Amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoylphenyl)acetamide

HRID 889401Notes

Reaction equation

HRID 889401 reaction equation
[NH2:1][C:2]1[N:3]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH:18]3[CH2:20][CH2:19]3)=[CH:10][CH:9]=2)[C:4]([SH:7])=[N:5][N:6]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](=[O:41])(=[O:40])[NH2:39])=[CH:34][C:33]=1[Cl:42])=[O:30]>CN(C=O)C>[NH2:1][C:2]1[N:3]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH:18]3[CH2:20][CH2:19]3)=[CH:10][CH:9]=2)[C:4]([S:7][CH2:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([S:38](=[O:41])(=[O:40])[NH2:39])=[CH:34][C:33]=2[Cl:42])=[O:30])=[N:5][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 215288302-chloro-N-(2-chloro-4-sulfamoylphenyl)acetamideHCID 178509206HCID 178509206, compound

Product 1

HCID 597636572-[5-Amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoylphenyl)acetamideYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a solution of 5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazole-3-thiol (708 mg, 2.5 mmol), K2CO3 (380 mg, 2.5 mmol) in DMF (20 mL) was added 2-chloro-N-(2-chloro-4sulfamoylphenyl)acetamide (710 mg, 2.5 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was evaporated. The residue was purified by silica gel chromatography to yield 2-[5-Amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoylphenyl)acetamide (1.26 g, 95%). 2-[5-Bromo-4-(4-cyclopropylnaphthalen-1-yl]-4H-[1,2,4]triazol-3-ylsulfannyl]-N-(2-chloro-4-sulfamoylphenyl)acetamide

Workup

  1. customUpon completion of the reaction
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2c231b8adcde497bbb1b2eda92a1241f
Source dataset
uspto-grants-2012_08
Patent number
US08252828B2

Reaction notes

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