Water → (2E)-1-[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one

HRID 896778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896778
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[C:15]([C:16](=[O:18])[CH3:17])=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.CO[CH:30](OC)[N:31]([CH3:33])[CH3:32]>>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:19]4[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=4)[C:15]([C:16](=[O:18])/[CH:17]=[CH:30]/[N:31]([CH3:33])[CH3:32])=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

4

Edukt 3

HCID 962WaterHCID 78373Dimethylformamide dimethyl acetalHCID 223500531-[7-(Cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone

Produkt 1

HCID 22350050(2E)-1-[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-oneAusbeute 93 %

Versuchsvorschrift

A solution of 1-[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone (5.56 g, 15.9 mmol) in N,N-dimethylformamide dimethyl acetal (25 mL) was heated at reflux for 5 days. The mixture was allowed to cool to room temperature. Water was added and the resulting mixture was extracted with ethyl acetate. The organic phase was dried (magnesium sulfate), filtered and concentrated. The resulting residue was purified by flash chromatography (7:3 ethyl acetate:acetone) to give (2E)-1-[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one (5.97 g, 93%) as a colored syrup: 1H NMR (CDCl3): δ 7.96-7.59 (m, 3H), 7.53 (d, 1H), 7.23 (dd, 1H), 6.93 (d, 2H), 5.97-5.94 (m, 2H), 5.07 (d, 1H), 3.95 (m, 1H), 3.81 (s, 3H), 3.0-2.3 (m, 6H), 2.07 (m, 2H), 1.76-1.60 (m, 6H); MS m/z 405 (M+1).

Aufarbeitung

  1. temperatureat reflux for 5 days
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography (7:3 ethyl acetate:acetone)

Quellen und Nachweise

ORD-Eintrag
ord-fa2ca958b42a45648d368478b874fd17
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919352B2

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