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Hydrochloric Acid → (E)-N-(1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-(6-amino-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

HRID 1297466
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1297466
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][N:12]([CH3:42])[C:13](=[O:41])/[CH:14]=[CH:15]/[C:16]2[CH:17]=[N:18][C:19]3[NH:20][C:21](=[O:40])[CH:22]([N:26]=C(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:23][C:24]=3[CH:25]=2)=[CH:3]1.Cl.[OH-].[Na+]>O1CCOCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][N:12]([CH3:42])[C:13](=[O:41])/[CH:14]=[CH:15]/[C:16]2[CH:17]=[N:18][C:19]3[NH:20][C:21](=[O:40])[CH:22]([NH2:26])[CH2:23][C:24]=3[CH:25]=2)=[CH:3]1
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Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23574461(E)-N-(1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-[6-(benzhydrylideneamino)-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]acrylamide

Produkt 1

HCID 10340289(E)-N-(1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-(6-amino-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of (E)-N-(1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-[6-(benzhydrylideneamino)-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]acrylamide (0.5 g, 0.9 mmole) in dioxane (15 mL) was added 1 N HCl (10 mL) with stirring at RT. After approximately 5 min the suspension cleared up then gradually reformed. After stirring for 1 h the reaction was neutralized with 1 N NaOH (10 mL) and concentrated to near dryness under vacuum. The resulting suspension was diluted with H2O (20 mL) and filtered, and the solid was rinsed with cold H2O and dried under vacuum. The slightly pinkish solid was triturated with Et2O, filtered, and dried under vacuum to give the title compound (248 mg, 71%) as an off-white solid: MS (ES) m/e 390.4 (M+H)+.

Aufarbeitung

  1. stirringAfter stirring for 1 h the reaction
  2. concentrationconcentrated
  3. additionThe resulting suspension was diluted with H2O (20 mL)
  4. filtrationfiltered
  5. washthe solid was rinsed with cold H2O
  6. customdried under vacuum
  7. customThe slightly pinkish solid was triturated with Et2O
  8. filtrationfiltered
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5698fcce307843cba4b81f147f89e0fb
Quelldatensatz
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07250424B2

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