Hydrochloric Acid → HCID 59436104, Verbindung

HRID 1802506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802506
C([O:4][C:5]([C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[C:17]([Cl:19])[C:16]([NH:20][C:21]3[C:30]4[CH:31]=[CH:32][N:33]=[C:34]([O:35]CC)[C:29]=4[C:28]4[C:23](=[CH:24][CH:25]=[N:26][CH:27]=4)[N:22]=3)=[C:15]([Cl:38])[CH:14]=2)[N:9]=1)([CH3:7])[CH3:6])(=O)C.Cl>C1COCC1.C(OCC)(=O)C.C1COCC1>[Cl:38][C:15]1[CH:14]=[C:13]([C:10]2[N:9]=[C:8]([C:5]([OH:4])([CH3:7])[CH3:6])[O:12][N:11]=2)[CH:18]=[C:17]([Cl:19])[C:16]=1[NH:20][C:21]1[C:30]2[CH:31]=[CH:32][NH:33][C:34](=[O:35])[C:29]=2[C:28]2[C:23](=[CH:24][CH:25]=[N:26][CH:27]=2)[N:22]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 59435993HCID 59435993, Verbindung

Produkt 1

HCID 59436104HCID 59436104, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21939870Tetrahydrofuran ethyl acetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 1-(3-{3,5-dichloro-4-[(10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-yl)amino]phenyl}-1,2,4-oxadiazol-5-yl)-1-methylethyl acetate (63 mg, 0.11 mmol) in THF (3 mL) was added HCl (0.188 mL, 1.13 mmol, 6M in water) and the mixture was heated to 60° C. for 45 min in a sealed tube. After cooling to room temperature, the reaction was diluted with ethyl acetate/THF (3:1) and washed with saturated aqueous sodium bicarbonate, followed by brine. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with MeOH in dichloromethane to afford the title compound.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with MeOH in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-17188567b28b4e2e930d5d6d9f2a5931
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349865B2

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