Triethylamine → 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [2-(2,4-dichlorophenyl)-2-methoxyamino-1-methyl-ethyl]-amide

HRID 1873864Notes

Reaction equation

HRID 1873864 reaction equation
[F:1][CH:2]([F:12])[C:3]1[C:7]([C:8](Cl)=[O:9])=[CH:6][N:5]([CH3:11])[N:4]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH:21]([NH:25][O:26][CH3:27])[CH:22]([NH2:24])[CH3:23].C(N(CC)CC)C>ClCCl>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH:21]([NH:25][O:26][CH3:27])[CH:22]([NH:24][C:8]([C:7]1[C:3]([CH:2]([F:12])[F:1])=[N:4][N:5]([CH3:11])[CH:6]=1)=[O:9])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 59403298HCID 59403298, compound

Product 1

HCID 594032993-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [2-(2,4-dichlorophenyl)-2-methoxyamino-1-methyl-ethyl]-amideYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (86 mg, 0.44 mmol) in dichloromethane (1 ml) was added dropwise to a stirred solution of (110 mg, 0.44 mmol) 2-(2,4-dichloro-phenyl)-2-methoxyamino-1-methyl-ethylamine, which was prepared as described in example P4, and triethylamine (50 mg, 0.50 mmol) in dichloromethane (3 ml) at 0° C. The reaction mixture was stirred for 1 hr at ambient temperature then allowed to stand for 1 h. After removal of the solvent the residue was purified by flash chromatography over silica gel (eluant:hexane/ethyl acetate 3:7). 115 mg (64.1% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [2-(2,4-dichlorophenyl)-2-methoxyamino-1-methyl-ethyl]-amide was obtained in the form of a resin as a mixture of diastereomeres.

Workup

  1. customwas prepared
  2. waitto stand for 1 h
  3. customAfter removal of the solvent the residue
  4. customwas purified by flash chromatography over silica gel (eluant:hexane/ethyl acetate 3:7)

Sources & evidence

ORD record
ord-3e85ad06ff8a4459a6c00a066e56e2dd
Source dataset
uspto-grants-2012_11
Patent number
US08304444B2

Reaction notes

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