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Ethyl Acetate → N'-[3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-yl]-N,N-dimethylimidoformamide

HRID 456687
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 456687
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:15]([N:16]=[CH:17][N:18]([CH3:20])[CH3:19])[C:10]2=[N:9][C:8]=1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=O.Cl.[CH:30]1([NH:35][C:36]([NH2:38])=[NH:37])[CH2:34][CH2:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH:30]1([NH:35][C:36]2[N:38]=[C:5]([C:7]3[N:11]4[CH:12]=[CH:13][CH:14]=[C:15]([N:16]=[CH:17][N:18]([CH3:20])[CH3:19])[C:10]4=[N:9][C:8]=3[C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[CH:4]=[CH:3][N:37]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1
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Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 69548821N'-[3-[(2E)-3-(dimethylamino)-2-propenoyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-yl]-N,N-dimethylimidoformamideHCID 178479367HCID 178479367, Verbindung

Produkt 1

HCID 69549491N'-[3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-yl]-N,N-dimethylimidoformamide
Ausbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of N′-[3-[(2E)-3-(dimethylamino)-2-propenoyl]-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-8-yl]-N,N-dimethylimidoformamide (130 mg, 0.34 mmol) in N,N-dimethylformamide was added N-cyclopentylguanidine hydrochloride (168 mg, 1.02 mmol), followed by anhydrous potassium carbonate (140 mg, 1.02 mmol). The resulting solution was heated at 100° C. for 16 hours. Upon cooling to room temperature, ethyl acetate and water were added. The phases were separated and the organics were washed with brine. The aqueous layer was extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate) to give N′-[3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-8-yl]-N,N-dimethylimidoformamide (80 mg, 53%) as a solid. 1H NMR (CDCl3): δ 9.09 (broad s, 1H), 8.60 (s, 1H), 8.04 (d, 1H), 7.63 (q, 2H), 7.04 (t, 2H), 6.78 (m, 2H), 6.36 (d, 1H), 5.14 (d, 1H), 4.31 (m, 1H), 3.10 (s, 3H), 3.05 (s, 3H), 2.0–2.1 (m, 2H), 1.4–1.9 (m, 6H); MS m/z 444 (M+1).

Aufarbeitung

  1. temperatureUpon cooling to room temperature
  2. customThe phases were separated
  3. washthe organics were washed with brine
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f0cf492e05a94da5ac42f0506889884b
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07186714B2

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