Triethylamine → N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide

HRID 589302Notes

Reaction equation

HRID 589302 reaction equation
[F:1][CH:2]([F:13])[C:3]1[C:7]([C:8](Cl)=[O:9])=[C:6]([F:11])[N:5]([CH3:12])[N:4]=1.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH:22]([O:26][CH3:27])[CH:23]([NH2:25])[CH3:24].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH:22]([O:26][CH3:27])[CH:23]([NH:25][C:8]([C:7]1[C:3]([CH:2]([F:13])[F:1])=[N:4][N:5]([CH3:12])[C:6]=1[F:11])=[O:9])[CH3:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 529205085-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbonyl chlorideHCID 594032951-(2,4-Dichlorophenyl)-1-methoxypropan-2-amine

Product 1

HCID 67963548N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamideYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At ambient temperature, 233 mg (1.1 mmol) of 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl chloride and 234 mg (1 mmol) of 1-(2,4-dichlorophenyl)-1-methoxypropan-2-amine are dissolved in 10 ml of dichloromethane. 121 mg (1.2 mmol) of triethylamine are added and the reaction mixture is stirred for 4 hrs at ambient temperature. The mixture is diluted by 50 ml of ethyl acetate and successively washed by a 1 N solution of HCl (twice), a saturated solution of potassium carbonate (twice) and brine and dried over magnesium sulfate. The solvents are removed and the crude amide is purified by column chromatography on silica gel (gradient heptane/ethyl acetate) to yields 400 mg (97% yield) of N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide as a pale yellow solid (M+H=410).

Workup

  1. washsuccessively washed by a 1 N solution of HCl (twice), a saturated solution of potassium carbonate (twice) and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvents are removed
  4. customthe crude amide is purified by column chromatography on silica gel (gradient heptane/ethyl acetate)

Sources & evidence

ORD record
ord-70adf4c7930c4a1f822d953fccfe7f3f
Source dataset
uspto-grants-2016_01
Patent number
US09232799B2

Reaction notes

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