Hydrochloric Acid → {3'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-biphenyl-4-yl}-acetonitrile

HRID 1096000노트

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HRID 1096000 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]#[N:32])=[CH:26][CH:25]=2)[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:23])[C:9]([OH:22])([C:14]1[CH:15]=[N:16][C:17]([O:20]C)=[CH:18][CH:19]=1)[C:10]([F:13])([F:12])[F:11].Cl.O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]#[N:32])=[CH:26][CH:25]=2)[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:23])[C:9]([OH:22])([C:14]1[CH:19]=[CH:18][C:17](=[O:20])[NH:16][CH:15]=1)[C:10]([F:12])([F:11])[F:13]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 66699162{3'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-2-(6-methoxy-pyridin-3-yl)-1-methyl-propyl]-biphenyl-4-yl}-acetonitrile

생성물 1

HCID 66699113{3'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-biphenyl-4-yl}-acetonitrile수율 69.9%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a solution of {3′-chloro-4′-[3,3,3-trifluoro-2-hydroxy-2-(6-methoxy-pyridin-3-yl)-1-methyl-propyl]-biphenyl-4-yl}-acetonitrile (87 mg) in dioxane (2.8 ml) was added conc. aqueous HCl (0.31 ml). The mixture was stirred at 100° C. for 1.5 h. After cooling to room temperature, water was added and the mixture was extracted with EtOAc. The organic phase was concentrated to dryness and the product was purified by chromatography (SiO2, CH2Cl2/MeOH 1:0=>9:1) to give the title compound (59 mg) as a colorless solid. MS (m/e)=447.3 [M+H+].

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc
  3. concentrationThe organic phase was concentrated to dryness
  4. customthe product was purified by chromatography (SiO2, CH2Cl2/MeOH 1:0=>9:1)

출처 및 근거

ORD 기록
ord-081b673388e14027acdcab0ced9eb59b
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138189B2

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