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 1895173ノート

反応式

HRID 1895173 の反応式
[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

参加物

3

反応物 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496271HCID 178496271、化合物

生成物 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-carboxylate収率 37%

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c12f78e3054642708671c8151b7ee0f5
出典データセット
uspto-grants-2013_08
特許番号
US08513251B2

反応ノート

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