Phenylhydrazine → 1-[2-(Difluoromethoxy)phenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 1407277ノート

反応式

HRID 1407277 の反応式
[F:1][CH:2]([F:26])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13](=[O:18])[C:12]([C:19](=O)[CH:20]=[CH:21][N:22](C)C)=[N:11]1.[C:27]1([NH:33]N)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC(O)=O>[F:1][CH:2]([F:26])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13](=[O:18])[C:12]([C:19]2[N:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:22]=[CH:21][CH:20]=2)=[N:11]1

参加物

4

反応物 2

HCID 7516PhenylhydrazineHCID 667105041-[2-(Difluoromethoxy)phenyl]-3-[3-(dimethylamino)prop-2-enoyl]-5-methoxypyridazin-4(1H)-one

生成物 1

HCID 594362271-[2-(Difluoromethoxy)phenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one収率 68%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of 1-[2-(difluoromethoxy)phenyl]-3-[3-(dimethylamino)prop-2-enoyl]-5-methoxypyridazin-4(1H)-one (0.50 g, 1.369 mmol) and phenylhydrazine (0.269 mL, 2.74 mmol) in AcOH (5 mL) was refluxed for 2 h. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was diluted with AcOEt, washed successively with 1 M HCl aqueous solution, saturated NaHCO3 aqueous solution, and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with hexane/AcOEt (7/3-0/10) to give the title compound (0.38 g, 68% yield) as an off-white amorphous solid: 1H NMR (300 MHz, CDCl3): δ ppm 3.88 (3H, s), 6.37 (1H, t, J=72.3 Hz), 6.57 (1H, dd, J=8.1, 1.7 Hz), 7.09-7.16 (1H, m), 7.22-7.25 (2H, m), 7.34-7.42 (6H, m), 7.76-7.78 (2H, m). LC-MS (ESI) m/z 411 [M+H]+. Anal. Calcd. for C21H16F2N4O3: C, 61.15; H, 4.07; N, 13.79. Found: C, 61.23; H, 4.11; N, 13.71.

後処理

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with AcOEt
  3. washwashed successively with 1 M HCl aqueous solution, saturated NaHCO3 aqueous solution, and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with hexane/AcOEt (7/3-0/10)

出典と根拠

ORDレコード
ord-6efa532292af4c7ea27123776a402b64
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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