Triethylamine → HCID 67460233, compound

HRID 2043786Notes

Reaction equation

HRID 2043786 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([OH:10])=O)[N:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[C:15](Cl)(=O)C(Cl)=O.N1([C:27]2([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:31]=[N:30][NH:29][NH:28]2)CCCCC1.C([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])C>ClCCl.CN(C)C=O>[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:39]2[CH2:40][CH2:41][CH:15]([N:29]3[N:28]=[C:27]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:31]=[N:30]3)[CH2:43][CH2:42]2)=[O:10])[N:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 5961182-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acidHCID 67461567HCID 67461567, compound

Product 1

HCID 67460233HCID 67460233, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-acetic acid (0.23 g, 1.1 mmol) in dichloromethane (5 mL) was added oxalyl chloride (0.20 mL, 14 mmol) and one drop of N,N-dimethylformamide. After 45 minutes the reaction mixture was concentrated in vacuo and the resulting residue was dissolved in dichloromethane (10 mL). The reaction mixture was then added to a solution of ethyl 4-piperidinyl-2H-1,2,3-triazole-4-carboxylate (0.23 g) and triethylamine (0.20 mL, 1.4 mmol) in dichloromethane (10 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. The organic layer was washed with saturated aqueous sodium bicarbonate, dried (Na2SO4) and the solvent was removed with a rotary evaporator. The residue was purified by medium pressure liquid chromatography (MPLC) using 35 to 60% ethyl acetate in hexanes as eluant to afford 0.35 g of the title compound as a white solid.

Workup

  1. concentrationAfter 45 minutes the reaction mixture was concentrated in vacuo
  2. dissolutionthe resulting residue was dissolved in dichloromethane (10 mL)
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed with a rotary evaporator
  6. customThe residue was purified by medium pressure liquid chromatography (MPLC)

Sources & evidence

ORD record
ord-ad2aa245ba4b429eab8412cb8cb522c8
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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