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Triethylamine → HCID 67460233, 화합물

HRID 2043786
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HRID 2043786 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

HCID 67460233HCID 67460233, 화합물수율 83.1%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
촉매
HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ad2aa245ba4b429eab8412cb8cb522c8
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08586611B2

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