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

HRID 1677762ノート

反応式

HRID 1677762 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-ac61994c826d424797f17470b7c77301
出典データセット
uspto-grants-2011_08
特許番号
US08008302B2

反応ノート

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