Trifluoroacetic acid → 8-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-one

HRID 577485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577485
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:33])[C:20]([O:26][CH:27]([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:21][CH:22]=3)[C:17]2=[O:34])=[C:13]([CH3:35])[CH:12]=[C:11]([CH3:36])[N:10]=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:33][C:19]1[C:20]([O:26][CH:27]([CH3:32])[C:28]([F:31])([F:29])[F:30])=[CH:21][CH:22]=[C:23]2[C:18]=1[C:17](=[O:34])[N:16]([CH2:15][C:14]1[C:9](=[O:8])[NH:10][C:11]([CH3:36])=[CH:12][C:13]=1[CH3:35])[CH2:25][CH2:24]2

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 867237102-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-one

Produkt 1

HCID 867237118-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-oneAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-one (58b, 70 mg, 0.14 mmol) in CH2Cl2 (5 mL) was added TFA (1 mL) at room temperature. The resulting mixture was stirred at room temperature overnight. The mixture was concentrated under vacuum. The residue was purified by column chromatography (EtOAc) to give the title compound (Example 58, 20 mg, 34%) as a white solid. 1H NMR (400 MHz, chloroform): δ 11.16 (s, 1H), 7.08-7.05 (d, 1H), 7.00-6.98 (d, 1H), 5.94 (s, 1H), 4.75 (s, 2H), 4.57-4.54 (t, 1H), 3.55 (s, 2H), 2.77 (s, 2H), 2.33-2.25 (d, 6H), 1.55 (s, 3H); MS 428.9 [M+H].

Aufarbeitung

  1. concentrationThe mixture was concentrated under vacuum
  2. customThe residue was purified by column chromatography (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-241f7f74e12c497a94a43a71fd175f9b
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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