Methanol → HCID 58072381, 화합물

HRID 1895300노트

반응식

HRID 1895300 반응식
[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

참가 물질

8

반응물 4

HCID 887MethanolHCID 7516PhenylhydrazineHCID 10942334Sodium MethoxideHCID 58072182HCID 58072182, 화합물

생성물 1

HCID 58072381HCID 58072381, 화합물수율 39%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매2회HCID 962Water용매HCID 7865Methyl formate용매

실험 절차

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 15 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.

후처리

  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 15 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

출처 및 근거

ORD 기록
ord-c490bfdde078462cab003b6c8afc2ee8
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513251B2

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