Triethylamine → 5-Cyano-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]furan-2-carboxamide

HRID 337506노트

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HRID 337506 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:19][C:20]([CH:22]2[CH:26]=[CH:25][C:24](=NO)[O:23]2)=[O:21])[S:9][C:10]=1[C:11]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12].[CH2:29]([N:31](CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.C(=O)([O-])O.[Na+]>ClCCl>[C:29]([C:24]1[O:23][C:22]([C:20]([NH:19][C:8]2[S:9][C:10]([C:11]([CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[O:12])=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[N:7]=2)=[O:21])=[CH:26][CH:25]=1)#[N:31]

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 516892Sodium BicarbonateHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 86612469N-[4-(2-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]-5-(hydroxyimino)furan-2-carboxamide

생성물 1

HCID 231447485-Cyano-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]furan-2-carboxamide수율 63.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Compound 514 (2.08 g, 5.00 mmol) and triethylamine (0.836 mL, 6.00 mmol) were suspended in dichloromethane (20 mL), and 2-chloro-1,3-dimethylimidazolinium chloride (2.03 g, 12.0 mmol) was added thereto at 0° C. This was stirred at 0° C. for 30 minutes, and then triethylamine (0.836 mL, 6.00 mmol) was added thereto, followed by stirring at 0° C. for 5 minutes. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=49:1), followed by recrystallizing from a mixed solvent (3:1) of ethanol and water to afford the entitled Compound 515 (1.26 g, 63%) as a pale brown solid.

후처리

  1. customat 0° C
  2. stirringby stirring at 0° C. for 5 minutes
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=49:1)
  7. customby recrystallizing from a mixed solvent (3:1) of ethanol and water

출처 및 근거

ORD 기록
ord-7eb2c60dd15445609b9abfbe500e079d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889718B2

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