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Water → 1-(2-(4-((3,4-dihydro-2H-pyrano(2,3-c)pyridin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride

HRID 1510792
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1510792
[ClH:1].[O:2]1[C:7]2=[CH:8][N:9]=[C:10]([CH2:12][NH:13][CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]4[C:31]5[C:26](=[N:27][CH:28]=[C:29](F)[CH:30]=5)[CH:25]=[CH:24][C:23]4=[O:33])[CH2:16][CH2:15]3)[CH:11]=[C:6]2[CH2:5][CH2:4][CH2:3]1.C[O-].[Na+].CO.O.[C:40](OCC)(=[O:42])C>CO>[ClH:1].[O:2]1[C:7]2=[CH:8][N:9]=[C:10]([CH2:12][NH:13][CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]4[C:31]5[C:26](=[N:27][CH:28]=[C:29]([O:42][CH3:40])[CH:30]=5)[CH:25]=[CH:24][C:23]4=[O:33])[CH2:16][CH2:15]3)[CH:11]=[C:6]2[CH2:5][CH2:4][CH2:3]1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23694274Sodium methanolate methanolHCID 689273251-(2-(4-((3,4-dihydro-2H-pyrano(2,3-c)pyridin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one hydrochloride

Produkt 1

HCID 688927231-(2-(4-((3,4-dihydro-2H-pyrano(2,3-c)pyridin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of 60 mg of 1-(2-(4-((3,4-dihydro-2H-pyrano(2,3-c)pyridin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one hydrochloride in 2 mL of methanol, 60 mg of a 28% sodium methoxide/methanol solution, and the mixture was heated under reflux while stirring for 4 hours. Thereto were added water and ethyl acetate, the organic layer was separated, and the aqueous layer was saturated with sodium chloride, and then extracted with ethyl acetate twice. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. To the resultant residue, 1 mL of ethyl acetate was added, and 1 mL of a 4.0 mol/L hydrogen chloride/ethyl acetate solution was added at room temperature. The solvent was distilled off under reduced pressure, ethyl acetate was added to the resultant residue, and the solid was filtered off to obtain 31 mg of 1-(2-(4-((3,4-dihydro-2H-pyrano(2,3-c)pyridin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride as a yellow solid.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customthe organic layer was separated
  4. extractionextracted with ethyl acetate twice
  5. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the resultant residue, 1 mL of ethyl acetate was added
  8. addition1 mL of a 4.0 mol/L hydrogen chloride/ethyl acetate solution was added at room temperature
  9. distillationThe solvent was distilled off under reduced pressure, ethyl acetate
  10. additionwas added to the resultant residue
  11. filtrationthe solid was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-4636eb8c44ea4bba87341db125200f37
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08211908B2

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