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

HRID 927178

反応式

HRID 927178 の反応式
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

参加物

4

反応物 2

HCID 712705113,4-bis(Benzyloxy)-6-{2-[2-fluoro-4-(trifluoromethyl)phenyl]-ethynyl}pyridazine2 回HCID 1785188083-Hydroxy-6-(2-Phenylethyl)pyridazin-4(1h)-One

生成物 1

HCID 178518819HCID 178518819、化合物収率 29%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-48576914959d4acbba65ccfe8bb5ea6f
出典データセット
uspto-grants-2016_03
特許番号
US09290456B2

関連ノート

読み込み中…