Tetrahydrofuran → (E)-N-(3-Cyano-6-fluoro-5-hydroxy-2-methyl[1,1'-biphenyl]-4-yl)-3-phenyl-2-propenamide

HRID 17349

반응식

HRID 17349 반응식
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O1CCCC1.[NH2:17][C:18]1[C:25]([OH:26])=[C:24]([F:27])[C:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:22]([CH3:34])[C:19]=1[C:20]#[N:21].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:20]([C:19]1[C:22]([CH3:34])=[C:23]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:24]([F:27])=[C:25]([OH:26])[C:18]=1[NH:17][C:1](=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:21]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 660233-Phenylprop-2-enoyl chlorideHCID 516892Sodium BicarbonateHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

생성물 1

HCID 86630839(E)-N-(3-Cyano-6-fluoro-5-hydroxy-2-methyl[1,1'-biphenyl]-4-yl)-3-phenyl-2-propenamide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Under nitrogen atmosphere, cinnamoyl chloride (378 mg, 2.27 mmol) was dropwise added to a tetrahydrofuran solution (10 ml) of 2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-41) (500 mg, 2.06 mmol) and sodium hydrogencarbonate (399 mg, 4.75 mmol) cooled with ice, followed by stirring at room temperature for 17 hours and stirring at 60° C. for 1 hour. After cooling, ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure.

후처리

  1. temperaturecooled with ice
  2. stirringstirring at 60° C. for 1 hour
  3. temperatureAfter cooling
  4. washby washing with water and saturated brine
  5. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure

출처 및 근거

ORD 기록
ord-b6f53dcdba73465fa9aca3432bd28b74
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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