Methanol → HCID 58072381、化合物

HRID 1407288ノート

反応式

HRID 1407288 の反応式
[C:1]([C:5]1[C:10](=[O:11])[CH:9]=[CH:8][N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:6]=1)(=O)[CH2:2][CH3:3].[CH3:22][O-].[Na+].[C:25]1([NH:31][NH2:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CO>C(OC)=O.O.Cl>[CH3:3][C:2]1[CH:22]=[N:32][N:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:1]=1[C:5]1[C:10](=[O:11])[CH:9]=[CH:8][N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:6]=1

参加物

8

反応物 4

HCID 887MethanolHCID 7516PhenylhydrazineHCID 10942334Sodium MethoxideHCID 58072182HCID 58072182、化合物

生成物 1

HCID 58072381HCID 58072381、化合物収率 39%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒2 回HCID 962Water溶媒HCID 7865Methyl formate溶媒

実験手順

To a suspension of 3-propanoyl-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (384 mg, 1.30 mmol) in methyl formate (3.8 mL) was added NaOMe (28% in MeOH, 326 mg, 1.69 mmol) at room temperature. The mixture was stirred at room temperature for 3.5 h. The mixture was diluted with water and 1 M HCl aqueous solution, extracted with AcOEt, washed with brine, dried over Na2SO4, filtered, concentrated in vacuo and crystallized with AcOEt/hexane. To the solid were added phenylhydrazine (0.405 mL, 4.12 mmol) and MeOH (6.7 mL). The mixture was heated to reflux for 3.5 h. The mixture was diluted with 1 M HCl aqueous solution, extracted with AcOEt, washed with saturated NaHCO3 aqueous solution, dried over Na2SO4, filtered, concentrated in vacuo, purified by column chromatography on silica gel (hexane/AcOEt=50/50 to 0/100) and crystallized with AcOEt/heptane to yield the title compound (161 mg, 39% yield) as a pale yellow solid: mp 208-211° C. 1H NMR (DMSO-d6, 300 MHz): δ ppm 2.09 (3H, s), 6.62 (1H, d, J=8.0 Hz), 7.26-7.35 (3H, m), 7.35-7.44 (2H, m), 7.64-7.85 (5H, m), 8.95 (1H, d, J=8.2 Hz). Anal. Calcd for C21H15F3N4O: C, 63.63; H, 3.81; N, 14.14. Found: C, 63.46; H, 3.92; N, 13.98.

後処理

  1. extractionextracted with AcOEt
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customcrystallized with AcOEt/hexane
  7. temperatureThe mixture was heated
  8. temperatureto reflux for 3.5 h
  9. extractionextracted with AcOEt
  10. washwashed with saturated NaHCO3 aqueous solution
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. custompurified by column chromatography on silica gel (hexane/AcOEt=50/50 to 0/100)
  15. customcrystallized with AcOEt/heptane

出典と根拠

ORDレコード
ord-48de4d301e7e4760894f98ae4405811d
出典データセット
uspto-grants-2014_12
特許番号
US08916566B2

反応ノート

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