4-Cyano-3-fluorobenzyl bromide → 3-[3-(4-cyano-3-fluoro-benzyl)-3H-imidazol-4-yl]-propionic Acid

HRID 429064

반응식

HRID 429064 반응식
C[O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1.Br[CH2:32][C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[C:35]([F:41])[CH:34]=1>CCOC(C)=O>[C:37]([C:36]1[CH:39]=[CH:40][C:33]([CH2:32][N:7]2[C:6]([CH2:5][CH2:4][C:3]([OH:30])=[O:2])=[CH:10][N:9]=[CH:8]2)=[CH:34][C:35]=1[F:41])#[N:38]

참가 물질

4

반응물 2

HCID 27784664-Cyano-3-fluorobenzyl bromideHCID 10475868Methyl 3-(1-Tritylimidazol-4-yl) Propionate

생성물 1

HCID 183543083-[3-(4-cyano-3-fluoro-benzyl)-3H-imidazol-4-yl]-propionic Acid

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

1-Trityl-imidazole-4-propionic acid methyl ester (2.15 g, 5.42 mmol) and 4-bromomethyl-2-fluoro-benzonitrile, as described above in Step D, (1.16 g, 5.42 mmol) were dissolved in EtOAc (20 mL) and heated at 60° C. for 3 h. The precipitated solid was filtered off, and the filtrate was concentrated to 10 mL then heating at 60° C. was continued overnight. The precipitate was collected and combined with the first solid and heated at reflux in CH3OH (20 mL) for 5 h. The reaction mixture was concentrated to dryness and triturated with hexane to remove triphenylmethane. The residue was dissolved in THF (10 mL)-H2O (5 mL), treated with 1 N NaOH (5 mL) and stirred at ambient temperature for 16 h. The reaction mixture was neutralized with 1N HCl (5 mL), concentrated to remove the THF, then lyophilized to give the title compound.

후처리

  1. filtrationThe precipitated solid was filtered off
  2. concentrationthe filtrate was concentrated to 10 mL
  3. temperaturethen heating at 60° C.
  4. customThe precipitate was collected
  5. temperatureheated
  6. temperatureat reflux in CH3OH (20 mL) for 5 h
  7. concentrationThe reaction mixture was concentrated to dryness
  8. customtriturated with hexane
  9. customto remove triphenylmethane
  10. dissolutionThe residue was dissolved in THF (10 mL)-H2O (5 mL)
  11. additiontreated with 1 N NaOH (5 mL)
  12. concentrationconcentrated
  13. customto remove the THF

출처 및 근거

ORD 기록
ord-62da6c6b6916435fa45d900c7fc79670
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316436B1

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