2-Thiophenecarbonyl chloride → Tert-butyl 4-(5-(2-thienyl)-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylate

HRID 888203노트

반응식

HRID 888203 반응식
[OH:1][NH:2][C:3](=[NH:17])[N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=O.CCN(C(C)C)C(C)C>C(Cl)Cl>[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[O:1][N:2]=[C:3]([N:4]2[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:8][CH2:9]2)[N:17]=1

참가 물질

5

반응물 3

HCID 789282-Thiophenecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 178452346tert-butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylate

생성물 1

HCID 58487964Tert-butyl 4-(5-(2-thienyl)-1,2,4-oxadiazol-3-yl)piperazine-1-carboxylate수율 20%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a cold (0° C.) solution of tert-butyl 4-[(hydroxyamino)(imino)methyl]piperazine-1-carboxylate (8 g, 32.7 mmol) in anhydrous DCM (150 mL) was added thiophene-2-carbonyl chloride (4.8 g, 32.7 mmol) followed by DIEA (7.2 mL, 39.2 mmol). The reaction mixture was stirred at RT for 12 hours and then filtered. The filtrate was evaporated and the residue was refluxed in pyridine (100 mL) for 3 hours. The solvent was removed under vacuum and the residue was dissolved in DCM. The organic layer was washed with a 10% aq. solution of sodium bicarbonate, water, brine and dried. The solvent was concentrated and the residue was purified by chromatography (Pet. Ether/EtOAc 7/3) to give 2.2 g (20%) of The title compound as a solid. TLC-Pet ether/EtOAc (9/1): Rf=0.75. HPLC purity>97%.

후처리

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. temperaturethe residue was refluxed in pyridine (100 mL) for 3 hours
  4. customThe solvent was removed under vacuum
  5. dissolutionthe residue was dissolved in DCM
  6. washThe organic layer was washed with a 10% aq. solution of sodium bicarbonate, water, brine
  7. customdried
  8. concentrationThe solvent was concentrated
  9. customthe residue was purified by chromatography (Pet. Ether/EtOAc 7/3)

출처 및 근거

ORD 기록
ord-c015abd082ed4c13a5b11d2757071805
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247437B2

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