HCID 86643933、化合物 → HCID 59436162、化合物

HRID 1895151ノート

反応式

HRID 1895151 の反応式
[F:1][C:2]1([F:26])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14](=[O:19])[C:13]([C:20](N(OC)C)=[O:21])=[N:12]3)[C:4]=2[O:3]1.[CH3:27][Mg+].[Br-]>C1COCC1>[C:20]([C:13]1[C:14](=[O:19])[C:15]([O:17][CH3:18])=[CH:16][N:11]([C:10]2[C:4]3[O:3][C:2]([F:26])([F:1])[O:6][C:5]=3[CH:7]=[CH:8][CH:9]=2)[N:12]=1)(=[O:21])[CH3:27]

参加物

4

反応物 2

HCID 86643933HCID 86643933、化合物HCID 178418689HCID 178418689、化合物

生成物 1

HCID 59436162HCID 59436162、化合物収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 1-(2,2-difluoro-1,3-benzodioxol-4-yl)-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide (2.7 g, 7.2 mmol) in THF (70 mL) was added dropwise 1 M MeMgBr in THF (14 mL, 14 mmol) at −78° C. for 15 min. After stirring at −78° C. for 1 h, the mixture was quenched with 1 M HCl aqueous solution (30 mL). The mixture was warmed to room temperature and extracted with AcOEt. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound (2.3 g, 99% yield) as yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 2.69 (3H, s), 3.95 (3H, s), 7.17 (1H, dd, J=7.9, 1.1 Hz), 7.26-7.32 (1H, m), 7.55 (1H, dd, J=8.7, 1.1 Hz), 8.00 (1H, s).

後処理

  1. customthe mixture was quenched with 1 M HCl aqueous solution (30 mL)
  2. temperatureThe mixture was warmed to room temperature
  3. extractionextracted with AcOEt
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-26eab59139784dd0a25460c0b03f2742
出典データセット
uspto-grants-2013_08
特許番号
US08513251B2

反応ノート

読み込み中…