Dimethylformamide → 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-[3-(4-methyl-1-piperazinyl)propyl]-2H-pyridazin-3-one

HRID 985031

反応式

HRID 985031 の反応式
[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12][CH:13](C(OC(C)(C)C)=O)[C:14](OC(C)(C)C)=O)=[CH:8][C:7]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([F:36])[CH:29]=3)=[N:6]2)[CH2:3][CH2:2]1.[H-].[Na+].C(OC(C)(C)C)(=O)CC(OC(C)(C)C)=O.BrC[C:56]1[C:57](=O)[N:58]([CH2:71][CH:72]2CC2)N=C(C2C=CC(OC)=C(F)C=2)C=1.[CH3:76][N:77](C)C=O>O>[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12][CH2:13][CH2:14][N:58]3[CH2:57][CH2:56][N:77]([CH3:76])[CH2:72][CH2:71]3)=[CH:8][C:7]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([F:36])[CH:29]=3)=[N:6]2)[CH2:3][CH2:2]1

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 68324Di-tert-butyl malonateHCID 219916102-cyclopropylmethyl-4-[2,2-di(tert-butoxycarbonyl)ethyl]-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-oneHCID 219917104-bromomethyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one

生成物 1

HCID 101365362-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-[3-(4-methyl-1-piperazinyl)propyl]-2H-pyridazin-3-one収率 61.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Preparation of 2-cyclopropylmethyl-4-[2,2-di(tert-butoxycarbonyl)ethyl]-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one After 55% sodium hydride (322 mg, 7.38 mmol) was added to a solution of di-tert-butyl malonate (970 mg, 4.48 mmol) in N,N-dimethylformamide (10 mL), 4-bromomethyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one (1.8 g, 4.90 mmol) was added under ice-cold stirring. The reaction mixture was stirred at room temperature for 1 hour, poured into water, and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was isolated and purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to yield the title compound as a yellow powder (yield: 1.39 mg, 61.8%).

後処理

  1. additionwas added under ice-cold stirring
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was isolated
  7. custompurified by column chromatography on silica gel (hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-3270f71b374f4c5097157d83614e4987
出典データセット
uspto-grants-2005_03
特許番号
US06869954B2

関連ノート

読み込み中…