3,4-bis(Benzyloxy)-6-{2-[2-fluoro-4-(trifluoromethyl)phenyl]-ethynyl}pyridazine → HCID 178518819, 화합물

HRID 927178

반응식

HRID 927178 반응식
OC1C(=O)NN=C(CCC2C=CC=CC=2)C=1.C([O:24][C:25]1[N:26]=[N:27][C:28]([C:39]#[C:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][C:42]=2[F:51])=[CH:29][C:30]=1[O:31]CC1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[F:51][C:42]1[CH:43]=[C:44]([C:47]([F:49])([F:50])[F:48])[CH:45]=[CH:46][C:41]=1[CH2:40][CH2:39][C:28]1[CH:29]=[C:30]([OH:31])[C:25](=[O:24])[NH:26][N:27]=1

참가 물질

4

반응물 2

HCID 712705113,4-bis(Benzyloxy)-6-{2-[2-fluoro-4-(trifluoromethyl)phenyl]-ethynyl}pyridazine2회HCID 1785188083-Hydroxy-6-(2-Phenylethyl)pyridazin-4(1h)-One

생성물 1

HCID 178518819HCID 178518819, 화합물수율 29%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Prepared as described for 4-hydroxy-6-(2-phenylethyl)pyridazin-3(2H)-one (Example 1) from 3,4-bis(benzyloxy)-6-{2-[2-fluoro-4-(trifluoromethyl)phenyl]-ethynyl}pyridazine (Intermediate 70) except that THF was used as the solvent. The reaction was filtered through diatomaceous earth flushing with further tetrahydrofuran and concentrated in vacuo. The residue was purified by column chromatography (silica C18 cartridge; eluting with 0-65% acetonitrile in water with acid modifier). The appropriate fractions were combined and concentrated in vacuo to remove the acetonitrile before the aqueous portion was extracted with ethyl acetate (×2), dried (MgSO4) and concentrated in vacuo. The resulting solid was recrystallised from a mixture of methyl tert-butyl ether and heptane to afford 6-{2-[2-fluoro-4-(trifluoromethyl)phenyl]ethyl}-4-hydroxy-2,3-dihydropyridazin-3-one as a cream solid (29% yield).

후처리

  1. customPrepared
  2. filtrationThe reaction was filtered through diatomaceous earth
  3. customflushing with further tetrahydrofuran
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica C18 cartridge; eluting with 0-65% acetonitrile in water with acid modifier)
  6. concentrationconcentrated in vacuo
  7. customto remove the acetonitrile before the aqueous portion
  8. extractionwas extracted with ethyl acetate (×2)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customThe resulting solid was recrystallised from a mixture of methyl tert-butyl ether and heptane

출처 및 근거

ORD 기록
ord-48576914959d4acbba65ccfe8bb5ea6f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290456B2

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