4-[(4-fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid → 7-FLUORO-1-METHYL-1,4-DIHYDRO-9H-PYRAZOLO[4,3-b]QUINOLIN-9-ONE

HRID 2119616

反応式

HRID 2119616 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:17])[C:13]=2[C:14]([OH:16])=O)=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:8][C:9]3[CH:10]=[N:11][N:12]([CH3:17])[C:13]=3[C:14](=[O:16])[C:6]=2[CH:7]=1

参加物

3

反応物 1

HCID 129856934-[(4-fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid

生成物 1

HCID 129856947-FLUORO-1-METHYL-1,4-DIHYDRO-9H-PYRAZOLO[4,3-b]QUINOLIN-9-ONE収率 38%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

A suspension of 4-[(4-fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid (EXAMPLE 1, step 1, 280 mg, 1.19 mmol) in phosphorus oxychloride (6 ml) was refluxed for 3 h. After cooling to room temperature, the mixture was concentrated and dried in vacuo. The residue was dissolved in 50% aqueous acetic acid (6 ml) and refluxed for 8 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (200 ml), washed with saturated aqueous sodium bicarbonate (100 ml) and dried over magnesium sulfate. Removal of solvent and recrystallization from ethyl acetate gave 98 mg (38%) of the title compound as a solid.

後処理

  1. temperaturewas refluxed for 3 h
  2. concentrationthe mixture was concentrated
  3. customdried in vacuo
  4. dissolutionThe residue was dissolved in 50% aqueous acetic acid (6 ml)
  5. temperaturerefluxed for 8 h
  6. temperatureAfter cooling to room temperature
  7. additionthe mixture was diluted with ethyl acetate (200 ml)
  8. washwashed with saturated aqueous sodium bicarbonate (100 ml)
  9. dry with materialdried over magnesium sulfate
  10. customRemoval of solvent and recrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-62a4b5f19fdf44ce848d22e826021974
出典データセット
uspto-grants-2004_02
特許番号
US06686373B2

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