Dimethylformamide dimethyl acetal → Methyl 5-methoxy-4-oxo-1-(2,2,3,3,7-pentafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)-1,4-dihydropyridazine-3-carboxylate

HRID 1624645

반응식

HRID 1624645 반응식
[CH3:1][O:2][CH2:3][C:4](=[O:27])[C:5](=[N:10][NH:11][C:12]1[C:25]([F:26])=[CH:24][C:15]2[O:16][C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[O:19][C:14]=2[CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[CH3:28]OC(OC)N(C)C>>[CH3:1][O:2][C:3]1[C:4](=[O:27])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[N:10][N:11]([C:12]2[C:25]([F:26])=[CH:24][C:15]3[O:16][C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[O:19][C:14]=3[CH:13]=2)[CH:28]=1

참가 물질

3

반응물 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496271HCID 178496271, 화합물

생성물 1

HCID 59436286Methyl 5-methoxy-4-oxo-1-(2,2,3,3,7-pentafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)-1,4-dihydropyridazine-3-carboxylate수율 37%

실험 절차

A mixture of methyl 4-methoxy-3-oxo-2-[(2,2,3,3,7-pentafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)hydrazono]butanoate (6.84 g, 17.2 mmol) in N,N-dimethylformamide dimethyl acetal (68 mL) was heated to reflux for 2.5 h. The mixture was concentrated in vacuo, diluted with brine, extracted with EtOAc, dried over MgSO4, filtered, concentrated in vacuo and purified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100 and EtOAc/MeOH=100/0 to 70/30) and on basic silica gel (hexane/EtOAc=80/20 to 0/100 and EtOAc/MeOH=100/0 to 70/30) to yield the title compound (2.58 g, 37% yield) as a pale yellow solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.79 (3H, s), 3.83 (3H, s), 8.01 (1H, d, J=10.2 Hz), 8.16 (1H, d, J=7.2 Hz), 8.58 (1H, s).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 h
  3. concentrationThe mixture was concentrated in vacuo
  4. additiondiluted with brine
  5. extractionextracted with EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100 and EtOAc/MeOH=100/0 to 70/30) and on basic silica gel (hexane/EtOAc=80/20 to 0/100 and EtOAc/MeOH=100/0 to 70/30)

출처 및 근거

ORD 기록
ord-b5c7a813751d4e60a2abd5b136ef772e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778944B2

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