Water → Ethyl (4-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenoxy)acetate

HRID 861113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861113
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:28]4[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:27][CH2:26][CH2:25][CH2:24]5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:28]4[CH:29]=[CH:30][C:31]([O:34][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:32][CH:33]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1354695774-{7-(Cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenol

Produkt 1

HCID 10165790Ethyl (4-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenoxy)acetateAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 4-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenol (100 mg, 0.22 mmol) in acetone (10 mL) was added ethyl α-bromoacetate (49 μL, 0.44 mmol) and potassium carbonate (304 mg, 2.2 mmol). The mixture was heated to reflux for 3 hours. The reaction mixture was cooled to room temperature and water was added. The solution was extracted with ethyl acetate. The organics were dried (magnesium sulfate), filtered and concentrated, followed by purification with flash chromatography (1:1 ethyl acetate:hexanes) to give ethyl (4-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenoxy)acetate (85 mg, 71%) as a brown oil. 1H NMR (CDCl3): δ 7.94 (d, 1H), 7.70 (d, 1H), 7.55 (d, 2H), 7.23 (t, 1H), 6.95 (d, 2H), 6.25 (d, 1H), 5.98–5.95 (m, 2H), 5.13 (d, 1H), 4.62 (s, 2H), 4.31–4.21 (m, 3H), 3.94 (m, 1H), 2.07–1.99 (m, 4H), 1.75–1.46 (m, 12H), 1.28 (t, 3H); MS m/z 541 (M+1).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionThe solution was extracted with ethyl acetate
  4. dry with materialThe organics were dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customfollowed by purification with flash chromatography (1:1 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6bef238c7d154561bfc2008965ef5e07
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153855B2

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