Hydrochloric Acid → 4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzaldehyde

HRID 1920033

Reaktionsgleichung

Reaktionsgleichung von HRID 1920033
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[N:17][C:18]=3[C:28]3[CH:29]=[N:30][NH:31][CH:32]=3)[N:13]=2)=[CH:8][CH:7]=1.Cl>CN1C(=O)CCC1>[C:22]1([C:21]2[C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH:2]=[O:1])=[CH:11][CH:10]=3)=[N:13][C:14]3[C:19]([CH:20]=2)=[C:18]([C:28]2[CH:29]=[N:30][NH:31][CH:32]=2)[N:17]=[CH:16][CH:15]=3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 57500724HCID 57500724, Verbindung

Produkt 1

HCID 575007264-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridine (1-2) (1.0 g, 2.4 mmol) in NMP (25 mL) was added 6N HCl (10 mL). The reaction was heated at 80° C. for 1 hour. The reaction mixture was cooled to room temperature, slowly quenched into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum to give 4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzaldehyde (1-3) as a white solid. MS (M+H)+: calculated 377.42; found 377.51

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customslowly quenched into saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-286fe8e00f3b4f1482a70e9aeca62605
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168652B2

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