Dimethylformamide → 1-(2-Chloro-4-(trifluoromethoxy)phenyl)-N-(2-(2-fluorophenyl)-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

HRID 1478797Notes

Reaction equation

HRID 1478797 reaction equation
CN(C=O)C.C(Cl)(=O)C(Cl)=O.[Cl:12][C:13]1[CH:18]=[C:17]([O:19][C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:15][C:14]=1[N:24]1[C:28]([CH3:29])=[C:27]([C:30](O)=[O:31])[N:26]=[N:25]1.[NH2:33][C:34]1[C:35](=[O:48])[N:36]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[F:47])[N:37]([CH3:40])[C:38]=1[CH3:39].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[C:17]([O:19][C:20]([F:21])([F:23])[F:22])[CH:16]=[CH:15][C:14]=1[N:24]1[C:28]([CH3:29])=[C:27]([C:30]([NH:33][C:34]2[C:35](=[O:48])[N:36]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[F:47])[N:37]([CH3:40])[C:38]=2[CH3:39])=[O:31])[N:26]=[N:25]1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 431636614-Amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one2×HCID 1185132681-(2-Chloro-4-(trifluoromethoxy)phenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

Product 1

HCID 1185132771-(2-Chloro-4-(trifluoromethoxy)phenyl)-N-(2-(2-fluorophenyl)-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

DMF (43 μL, 0.56 mmol) was dissolved in DCM (1 mL) and cooled to 0° C. Oxalyl chloride (27 μL, 0.308 mmol) was added followed by 1-(2-chloro-4-(trifluoromethoxy)phenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (90 mg, 0.28 mmol) and the reaction mixture was stirred for 10 min. 4-Amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate B) (62 mg, 0.28 mmol) was added, followed by triethylamine (117 μL, 0.839 mmol). The reaction was allowed to warm to RT and stirred for 4 h. Saturated aqueous NaHCO3 was added to the reaction mixture and the product was extracted with DCM. The organic extract was dried and concentrated under reduced pressure. The crude material was purified by reversed phase chromatography (Prep Method G) to afford the title compound.

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 4 h
  3. extractionthe product was extracted with DCM
  4. extractionThe organic extract
  5. customwas dried
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by reversed phase chromatography (Prep Method G)

Sources & evidence

ORD record
ord-ca6026ef22694b47941df1f65619382e
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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