1,2-Dichloroethane → 1-[5-(3-methanesulfonylamino-2-methoxy-5-trifluoromethyl-phenylcarbamoyl)-2-methyl-phenyl]-1H-1,2,3-triazole-4-carboxylic Acid Methyl Ester

HRID 2099152Notes

Reaction equation

HRID 2099152 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[N:7][N:8]([C:10]2[CH:15]=[C:14]([C:16]([OH:18])=O)[CH:13]=[CH:12][C:11]=2[CH3:19])[CH:9]=1)=[O:4].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.[NH2:34][C:35]1[C:36]([O:50][CH3:51])=[C:37]([NH:45][S:46]([CH3:49])(=[O:48])=[O:47])[CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[N:7][N:8]([C:10]2[CH:15]=[C:14]([C:16](=[O:18])[NH:34][C:35]3[CH:40]=[C:39]([C:41]([F:43])([F:42])[F:44])[CH:38]=[C:37]([NH:45][S:46]([CH3:49])(=[O:48])=[O:47])[C:36]=3[O:50][CH3:51])[CH:13]=[CH:12][C:11]=2[CH3:19])[CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 22506980N-(3-amino-2-methoxy-5-trifluoromethyl-phenyl)-methanesulfonamideHCID 587848831-(5-carboxy-2-methyl-phenyl)-1H-1,2,3-triazole-4-carboxylic acid methyl ester

Product 1

HCID 104369241-[5-(3-methanesulfonylamino-2-methoxy-5-trifluoromethyl-phenylcarbamoyl)-2-methyl-phenyl]-1H-1,2,3-triazole-4-carboxylic Acid Methyl EsterYield 5.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

1-(5-Carboxy-2-methyl-phenyl)-1H-1,2,3-triazole-4-carboxylic acid methyl ester (26 mg, 0.101 mmol) was stirred with 21 mg (0.153 mmol) of 1-hydroxy-7-azabenzotriazole (HOAt) in 1 mL of DMF and 24 mg (0. 126 mmol) of EDC was added. After 1 h of stirring at about 10° C., 30 mg (0.106 mmol) of N-(3-amino-2-methoxy-5-trifluoromethyl-phenyl) -methanesulfonamide was added. The mixture was stirred overnight then heated to 60° C. for 6 h. The reaction was then cooled and water was added. The precipitate was collected and chromatographed twice by preparative TLC (5% MeOH in CH2Cl2) and once by flash chromatography (0-4.5% MeOH in dichloromethane). The pure fractions yielded 3 mg (5.6%) of the title compound. ESI MS (m/z 526, 100, M−H).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred overnight
  3. temperaturethen heated to 60° C. for 6 h
  4. temperatureThe reaction was then cooled
  5. customThe precipitate was collected
  6. customchromatographed twice by preparative TLC (5% MeOH in CH2Cl2) and once by flash chromatography (0-4.5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-f083ea2e7e6a4a5799bc6f63d77de78a
Source dataset
uspto-grants-2009_08
Patent number
US07569568B2

Reaction notes

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