4-[(4-benzylphenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid → 7-Benzyl-1-methyl-1,4-dihydro-pyrazolo[4,3-b]quinolin-9-one

HRID 2119625

반응식

HRID 2119625 반응식
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:16]=[N:17][N:18]([CH3:23])[C:19]=2[C:20]([OH:22])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[NH:14][C:15]3[CH:16]=[N:17][N:18]([CH3:23])[C:19]=3[C:20](=[O:22])[C:12]=2[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

3

반응물 1

HCID 234423114-[(4-benzylphenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid

생성물 1

HCID 98571507-Benzyl-1-methyl-1,4-dihydro-pyrazolo[4,3-b]quinolin-9-one수율 84.4%

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

A mixture of 4-[(4-benzylphenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid (EXAMPLE 11, step 1, 4.86 g, 15.81 mmol) in phosphorus oxychloride (40 ml) was refluxed for 3 h. After cooling to room temperature, the mixture was concentrated and dried in vacuo. The mixture was dissolved in ethyl acetate (300 ml), washed with water (100 ml) and saturated aqueous sodium bicarbonate (100 ml×2) and dried over magnesium sulfate. Removal of solvent gave the dark red residue, which was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1/3) to afford 3.86 g (79%) of the title compound as a yellow solid.

후처리

  1. temperaturewas refluxed for 3 h
  2. concentrationthe mixture was concentrated
  3. customdried in vacuo
  4. dissolutionThe mixture was dissolved in ethyl acetate (300 ml)
  5. washwashed with water (100 ml) and saturated aqueous sodium bicarbonate (100 ml×2)
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of solvent
  8. customgave the dark red residue, which
  9. customwas chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1/3)

출처 및 근거

ORD 기록
ord-1a7709c33ba34c6d86aaaa5e3f9ac4e8
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06686373B2

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