2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one → 8-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one

HRID 577545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577545
C([O:8][C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[C:19]([Cl:30])[C:20]([O:26][CH:27]([CH3:29])[CH3:28])=[N:21][CH:22]=3)[C:17]2=[O:31])=[C:13]([CH3:32])[CH:12]=[C:11]([CH3:33])[N:10]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:30][C:19]1[C:20]([O:26][CH:27]([CH3:29])[CH3:28])=[N:21][CH:22]=[C:23]2[C:18]=1[C:17](=[O:31])[N:16]([CH2:15][C:14]1[C:9](=[O:8])[NH:10][C:11]([CH3:33])=[CH:12][C:13]=1[CH3:32])[CH2:25][CH2:24]2

Komponenten

3

Edukt 1

HCID 867237742-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one

Produkt 1

HCID 867237758-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one (112f, 22 mg, 0.05 mmol) in TFA (2 mL) was stirred at room temperature for 24 hours. Volatiles were removed under vacuum and the residue was diluted in MeOH (1 mL). The solution was neutralized by 7N NH3 in MeOH (1.5 mL) and the product was purified by prep TLC (100% EtOAc) to afford the title compound as a white solid (Example 112, 8 mg, 50%). 1H NMR (400 MHz, DMSO-d6) δ 1.30 (s, 3H) 1.32 (s, 3H) 2.12 (s, 3H) 2.15 (s, 3H) 2.75 (t, J=6.17 Hz, 2H) 3.43 (t, J=6.17 Hz, 2H) 4.56 (s, 2H) 5.21-5.30 (m, 1H) 5.88 (s, 1H) 8.02 (s, 1H) 11.56 (br. s., 1H); MS 376.2 [M+1].

Aufarbeitung

  1. customVolatiles were removed under vacuum
  2. additionthe residue was diluted in MeOH (1 mL)
  3. customthe product was purified by prep TLC (100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-d77280f499a445f98036c22ff4da50ef
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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