Triethylamine → HCID 50997446, compound

HRID 1807375Notes

Reaction equation

HRID 1807375 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][O:11][CH3:12])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[F:20][CH:21]([F:31])[C:22]1[C:26]([C:27](Cl)=[O:28])=[CH:25][N:24]([CH3:30])[N:23]=1>ClCCl.O>[I:1][C:2]1[CH:3]=[C:4]([CH:8]([N:10]([O:11][CH3:12])[C:27]([C:26]2[C:22]([CH:21]([F:31])[F:20])=[N:23][N:24]([CH3:30])[CH:25]=2)=[O:28])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 50995121HCID 50995121, compound

Product 1

HCID 50997446HCID 50997446, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[1-(3-iodo-phenyl)-ethyl]-O-methyl-hydroxylamine (3 g, 10.8 mmol), prepared as described in example P11, in dichloromethane (30 ml), was added triethylamine (2.5 ml, 26.3 mmol) followed by a solution of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (2.2 g, 11.3 mmol) slowly at 0° C. After complete addition of acid chloride, the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was diluted with water (100 ml) and extracted with dichloromethane (3×60 ml). The combined dichloromethane layer was washed with 2N HCl, sat. NaHCO3 and brine, dried over anh. sodium sulfate and concentrated. The crude mass was purified by column chromatography using 35% ethyl acetate in hexane to yield 2.7 g (60% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [1-(3-iodo-phenyl)-ethyl]methoxy-amide in form of a solid. Mp 136-138° C.

Workup

  1. extractionextracted with dichloromethane (3×60 ml)
  2. washThe combined dichloromethane layer was washed with 2N HCl, sat. NaHCO3 and brine
  3. dry with materialdried over anh. sodium sulfate
  4. concentrationconcentrated
  5. customThe crude mass was purified by column chromatography

Sources & evidence

ORD record
ord-459b16f100ea403ba66fc65ced8e7e39
Source dataset
uspto-grants-2013_01
Patent number
US08357634B2

Reaction notes

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