Ethyl 3-(2-fluorophenyl)-3-oxopropanoate → HCID 178515544, 화합물

HRID 17827

반응식

HRID 17827 반응식
[CH:1]1([C:4]2[CH:5]=[C:6]([NH2:9])[NH:7][N:8]=2)[CH2:3][CH2:2]1.C([O:12][C:13](=O)[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])=O)C>CC(O)=O>[CH:1]1([C:4]2[CH:5]=[C:6]3[NH:9][C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[F:23])=[CH:14][C:13](=[O:12])[N:7]3[N:8]=2)[CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 296342Ethyl 3-(2-fluorophenyl)-3-oxopropanoateHCID 178507266HCID 178507266, 화합물

생성물 1

HCID 178515544HCID 178515544, 화합물

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

5-Cyclopropyl-2H-pyrazol-3-ylamine (2.9 g, 0.0235 mol) was suspended in AcOH (18 ml), 3-(2-fluorophenyl)-3-oxopropionic acid ethyl ester (4.67 ml, 1.1 eq) was added and the mixture heated at reflux for 3 h. The mixture was cooled to rt and concentrated underreduced pressure. The residue was stirred with EtOAc and the solid collected by filtration to give 2 g of 2-cyclopropyl-5-(2-fluorophenyl)-4H-pyrazolo[1,5-a]pyrimidin-7-one. Step B: The compound from step A (1 g, 0.00371 mol) was dissolved in POCl3 (12 ml) and cooled to 0° C. N,N-dimethylaniline (1.4 ml, 3 eq) was added and the mixture heated at 80° C. for 16 h. The mixture was cooled to rt and the volatiles removed. The resulting residue was dissolved in CH2Cl2, poured onto ice, and taken to pH 8 with NaHCO3 (s). The CH2Cl2 layer was removed, washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, hexane-EtOAc/hexane 1:9) to give 0.85 g of the title compound. LCMS: MH+=288.1.

후처리

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated underreduced pressure
  4. filtrationthe solid collected by filtration

출처 및 근거

ORD 기록
ord-bfbb1a8bfbbb4d4f994bce1798bea719
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741318B2

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