Dimethylformamide → 1-(2,4-Dichlorophenyl)-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 1478793Notes

Reaction equation

HRID 1478793 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=O)[N:11]=[N:10]1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[NH2:29][C:30]1[C:31](=[O:44])[N:32]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[F:43])[N:33]([CH3:36])[C:34]=1[CH3:35].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([CH3:14])=[C:12]([C:15]([NH:29][C:30]2[C:31](=[O:44])[N:32]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[F:43])[N:33]([CH3:36])[C:34]=2[CH3:35])=[O:17])[N:11]=[N:10]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 3021721-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acidHCID 431636614-Amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one2×

Product 1

HCID 1185132981-(2,4-Dichlorophenyl)-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 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (100 mg, 0.368 mmol), oxalyl chloride (0.048 ml, 0.551 mmol) and DMF (0.057 ml, 0.735 mmol) in DCM (5 ml) was stirred at RT for 15 mins. 4-Amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate B) (89 mg, 0.404 mmol) was added followed by triethylamine (0.154 ml, 1.103 mmol) and the mixture was stirred at RT for 30 mins. The resulting mixture was diluted with DCM, washed with 0.1M HCl(aq) and sat. NaHCO3(aq) and the organic extracts were passed through a phase separating cartridge and concentrated under reduced pressure. The resultant brown oil was absorbed onto silica and purified by chromatography eluting with 0-10% MeOH in TBME. The product fractions were combined and concentrated under reduced pressure to give a pale pink solid which was triturated with diethylether. The resulting solid was collected by filtration and dried in the vacuum oven to give the title compound as a pale pink solid.

Workup

  1. washwashed with 0.1M HCl(aq) and sat. NaHCO3(aq)
  2. customseparating cartridge
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant brown oil was absorbed onto silica
  5. custompurified by chromatography
  6. washeluting with 0-10% MeOH in TBME
  7. concentrationconcentrated under reduced pressure
  8. customto give a pale pink solid which
  9. customwas triturated with diethylether
  10. filtrationThe resulting solid was collected by filtration
  11. customdried in the vacuum oven

Sources & evidence

ORD record
ord-9cc27333110747e5a8f13fa4e80620f9
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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