p-Toluenesulfonic acid → Ethyl 4-(2-chlorophenyl)-4,7-dihydro-2-methyl-6-propyl-2H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 489402

반응식

HRID 489402 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[C:9]([C:15](=O)[CH2:16][CH2:17][CH3:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[NH2:20][C:21]1[CH:25]=[CH:24][N:23]([CH3:26])[N:22]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:15]([CH2:16][CH2:17][CH3:18])[NH:20][C:21]2=[N:22][N:23]([CH3:26])[CH:24]=[C:25]12

참가 물질

6

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 1372541-Methyl-3-aminopyrazoleHCID 69733996Ethyl 2-(2-chlorophenyl)methylene-3-oxohexanoate

생성물 1

HCID 135583757Ethyl 4-(2-chlorophenyl)-4,7-dihydro-2-methyl-6-propyl-2H-pyrazolo[3,4-b]pyridine-5-carboxylate

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 1140Toluene용매

실험 절차

A solution of ethyl 3-ketohexanoate (7.5 g), 2-chlorobenzaldehyde (6.6 g), piperidine (1.2 g) and acetic acid (2.25 g) in benzene (50 ml) was heated under reflux for 5 hours, and the reaction mixture was dehydrated using a Dean-Stark condenser. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography using an eluent (hexane-ethyl acetate (3:1)) to give ethyl 2-(2-chlorophenyl)methylen-3-oxohexanoate ((E)/(Z)=1:1 mixture) as a yellow oil. A solution of ethyl 2-(2-chlorophenyl)methylene-3-oxohexanoate ((E)/(Z)=1:1 mixture, 2.8 g), 3-amino-1-methylpyrazole (0.25 g) and p-toluenesulfonic acid (25 mg) in toluene (5 mL) and dimethylsulfoxide (0.5 mL) was heated under reflux for one day. The solvent was evaporated under reduced pressure, and the mixture was extracted with ethyl acetate (10 mL) and washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give an oil. The obtained oil was purified by silica gel column chromatography (eluent (ethyl acetate-methanol (10:1))) to give the title compound as colorless crystals.

후처리

  1. temperatureunder reflux for one day
  2. customThe solvent was evaporated under reduced pressure
  3. extractionthe mixture was extracted with ethyl acetate (10 mL)
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customto give an oil
  8. customThe obtained oil was purified by silica gel column chromatography (eluent (ethyl acetate-methanol (10:1)))

출처 및 근거

ORD 기록
ord-74f1caa266ea4da288617841a066fc2c
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977262B2

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