Ethylacetate methanol → Methyl 1-(4-bromo-2,5-difluorophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylate

HRID 1624693

反応式

HRID 1624693 の反応式
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][N:10]=[C:11]([C:16](=[O:20])[CH2:17][O:18][CH3:19])[C:12]([O:14][CH3:15])=[O:13])=[C:4]([F:21])[CH:3]=1.[CH3:22]COC(C)=O.CO>COC(OC)N(C)C>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[CH:22]=[C:17]([O:18][CH3:19])[C:16](=[O:20])[C:11]([C:12]([O:14][CH3:15])=[O:13])=[N:10]2)=[C:4]([F:21])[CH:3]=1

参加物

4

反応物 2

HCID 21584119Ethylacetate methanolHCID 178496284methyl 2-[(4-bromo-2,5-difluorophenyl)hydrazinylidene]-4-methoxy-3-oxobutanoate

生成物 1

HCID 58072213Methyl 1-(4-bromo-2,5-difluorophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylate収率 83%

試薬・触媒・溶媒 1

HCID 78373Dimethylformamide dimethyl acetal溶媒

実験手順

A solution of methyl 2-[(4-bromo-2,5-difluorophenyl)hydrazono]-4-methoxy-3-oxobutanoate (33 g, 90 mmol) in N,N-dimethylformamide dimethyl acetal (72 mL) was stirred at 110° C. for 3 h. After cooling to room temperature, the mixture was concentrated under reduce pressure. To the residue were added MeOH and silica gel The mixture was evaporated and purified by silica gel column chromatography eluting with hexane/AcOEt (1/0 to 0/1) and then AcOEt/MeOH (4/1) to give the title compound (27.9 g, 83% yield) as a brown gum: 1H NMR (300 MHz, DMSO-d5): δ ppm 3.80 (3H, s), 3.83 (3H, s), 8.01 (1H, dd, J=8.7, 6.8 Hz), 8.15 (1H, dd, J=9.8, 6.0 Hz), 8.55 (1H, d, J=1.5 Hz). LC-MS (ESI) m/z 376 [M+H]+.

後処理

  1. concentrationthe mixture was concentrated
  2. additionTo the residue were added MeOH and silica gel The mixture
  3. customwas evaporated
  4. custompurified by silica gel column chromatography
  5. washeluting with hexane/AcOEt (1/0 to 0/1)

出典と根拠

ORDレコード
ord-8fdc7721c46844c3a08ae79b4a2d6d8d
出典データセット
uspto-grants-2014_07
特許番号
US08778944B2

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