Triethylamine → HCID 131730167, compound

HRID 1807385Notes

Reaction equation

HRID 1807385 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]1[CH2:10][C@H:9]1[CH:11]([NH:13][O:14][CH3:15])[CH3:12].C(N(CC)CC)C.[F:23][CH:24]([F:34])[C:25]1[C:29]([C:30](Cl)=[O:31])=[CH:28][N:27]([CH3:33])[N:26]=1>ClCCl.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]1[CH2:10][C@H:9]1[CH:11]([N:13]([O:14][CH3:15])[C:30]([C:29]1[C:25]([CH:24]([F:34])[F:23])=[N:26][N:27]([CH3:33])[CH:28]=1)=[O:31])[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 86669067HCID 86669067, compound

Product 1

HCID 131730167HCID 131730167, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of trans N-{1-[2-(2-chloro-phenyl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine (0.30 g; 1.3 mmol) prepared as described in example P12 and triethylamine (0.25 ml; 1.7 mmol) in dichloromethane (5.0 ml) at ambient temperature was added dropwise 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (0.28 g; 1.3 mmol). The reaction mixture was stirred for 16 hours at ambient temperature then poured in water (50 ml) and extracted with dichloromethane (3×25 ml). Combined organic layers were washed with water (10 ml), brine and dried over anhydrous sodium sulphate. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel (elution gradient: cyclohexane/ethyl acetate 99:1 to 1:99) to afford 0.46 g (92% of theory) of trans 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid {1-[2-(2-chloro-phenyl)-cyclopropyl]-ethyl}-methoxy-amide as single diastereomere A in form of a clear viscous oil.

Workup

  1. extractionextracted with dichloromethane (3×25 ml)
  2. washCombined organic layers were washed with water (10 ml), brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by flash chromatography over silica gel (elution gradient: cyclohexane/ethyl acetate 99:1 to 1:99)

Sources & evidence

ORD record
ord-8f85892659bf41ed806f333a5c42ffcd
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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