Imidazole → 5-Amino-3-(4-sulfamoyl-phenylamino)-[1,2,4]triazole-1-carbothioic acid (4-phenoxy-phenyl)-amide

HRID 1179263Notes

Reaction equation

HRID 1179263 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].[O:13]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CN=C1.[NH2:32][C:33]1[NH:37][N:36]=[C:35]([NH:38][C:39]2[CH:44]=[CH:43][C:42]([S:45]([NH2:48])(=[O:47])=[O:46])=[CH:41][CH:40]=2)[N:34]=1>C(#N)C.CN(C=O)C>[O:13]([C:20]1[CH:21]=[CH:22][C:23]([NH:24][C:1]([N:37]2[C:33]([NH2:32])=[N:34][C:35]([NH:38][C:39]3[CH:40]=[CH:41][C:42]([S:45](=[O:46])(=[O:47])[NH2:48])=[CH:43][CH:44]=3)=[N:36]2)=[S:2])=[CH:25][CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8764(4-Aminophenoxy)benzeneHCID 802641,1'-ThiocarbonyldiimidazoleHCID 113797954-((3-amino-1H-1,2,4-triazol-5-yl)amino)benzenesulfonamide

Product 1

HCID 589764675-Amino-3-(4-sulfamoyl-phenylamino)-[1,2,4]triazole-1-carbothioic acid (4-phenoxy-phenyl)-amideYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Thiocarbonyldiimidazole (0.56 mmol, 1.5 equivalent) was added to a solution of 4-phenoxy aniline (0.6 mmol, 1.6 equivalents) and imidazole (0.07 mmol, 0.2 equivalent) in acetonitrile (5 ml). The reaction mixture was stirred at room temperature for three hours. 4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-benzenesulfonamide (0.37 mM, 1 equivalent) was added in one portion. The reaction mixture was stirred at 50° C. for 16 hours. After addition of DMF (1 ml), the reaction mixture was stirred at 80° C. for one hour. The reaction mixture was concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with EtOAc:pentane (30:70 to 0:100) to afford the title compound (40 mg; 40% yield). 1H NMR (400 MHz, DMSO-d6) 7.05-7.18 (6H, m), 7.20-7.23 (1H, t), 7.40-7.50 (4H, m), 7.70-7.75 (2H, d), 7.80-7.85 (2H, d), 8.45-8.50 (2H, s), 9.80-9.85 (1H, s), 10.90 (1H, s); MS (ES+) m/e=482

Workup

  1. stirringThe reaction mixture was stirred at 50° C. for 16 hours
  2. stirringthe reaction mixture was stirred at 80° C. for one hour
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with EtOAc:pentane (30:70 to 0:100)

Sources & evidence

ORD record
ord-c0fad69b0d2b47a5b0a3e25387f6e622
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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