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Acetic Acid → Ethyl 1-[(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)methyl]-4-piperidinecarboxylate

HRID 1942586
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HRID 1942586 반응식
[CH2:1]([C:3]1[C:10]([C:11]2[S:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=3)=[N:14][N:15]=2)=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O)[CH3:2].[NH:30]1[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]1.CC(O)=O>C(O)C>[CH2:1]([C:3]1[C:10]([C:11]2[S:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:24])[CH3:25])=[C:18]([C:26]([F:28])([F:29])[F:27])[CH:17]=3)=[N:14][N:15]=2)=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][N:30]1[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]1)[CH3:2]
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참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 70770Ethyl 4-piperidinecarboxylateHCID 866589982-Ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}benzaldehyde

생성물 1

HCID 66981714Ethyl 1-[(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)methyl]-4-piperidinecarboxylate수율 99.9%

시약·촉매·용매 1

HCID 702
Ethanol
용매

실험 절차

To a solution of 2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}benzaldehyde (D6) (54 mg) and ethyl 4-piperidinecarboxylate (101 mg) in ethanol (10 mL) stirred at room temperature was added AcOH (0.037 mL). The reaction mixture was stirred at room temperature for 10 min. Then the solvent was removed by evaporation. To the residue was added dichloromethane (DCM) (10 mL) and sodium triacetoxyborohydride (82 mg). Stirring continued for 2 h. Water was added to quench the reaction, and DCM was removed by evaporation. The mixture was extracted by EA for 3 times. The combined organic phases were washed by brine, dried over anhydrous Na2SO4. The dried solution was filtered and concentrated to afford the crude product ethyl 1-[(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)methyl]-4-piperidinecarboxylate (D7) (72.1 mg). MS (ES): C29H34F3N3O3S requires 561. found 562.1 (M+H+).

후처리

  1. customThen the solvent was removed by evaporation
  2. additionTo the residue was added dichloromethane (DCM) (10 mL) and sodium triacetoxyborohydride (82 mg)
  3. stirringStirring
  4. waitcontinued for 2 h
  5. additionWater was added
  6. customto quench
  7. customthe reaction, and DCM
  8. customwas removed by evaporation
  9. extractionThe mixture was extracted by EA for 3 times
  10. washThe combined organic phases were washed by brine
  11. dry with materialdried over anhydrous Na2SO4
  12. filtrationThe dried solution was filtered
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-25e379eb5b8e45f18daed6c728ff9488
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08389508B2

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