2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one → 8-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 577509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577509
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:32])[C:20]([C:26]4[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=4)=[CH:21][CH:22]=3)[C:17]2=[O:33])=[C:13]([CH3:34])[CH:12]=[C:11]([CH3:35])[N:10]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:32][C:19]1[C:20]([C:26]2[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=2)=[CH:21][CH:22]=[C:23]2[C:18]=1[C:17](=[O:33])[N:16]([CH2:15][C:14]1[C:9](=[O:8])[NH:10][C:11]([CH3:35])=[CH:12][C:13]=1[CH3:34])[CH2:25][CH2:24]2

Komponenten

3

Edukt 1

HCID 867237352-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one

Produkt 1

HCID 867237368-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-oneAusbeute 17,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one (66c, 60 mg, 0.12 mmol) in TFA (3 mL) was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue purified by prep chromatography to give the title compound (Example 66, 8.5 mg, 17%) as a white solid. 1H NMR (700 MHz, DMSO-d6) δ 11.56 (br. s, 1H) 7.44 (d, J=7.70 Hz, 1H) 7.35 (d, J=7.70 Hz, 1H) 7.50 (d, J=1.76 Hz, 1H) 6.29 (d, J=1.76 Hz, 1H) 5.90 (s, 1H) 4.60 (s, 2H) 3.61 (s, 3H) 3.46-3.50 (m, 2H) 2.91 (t, J=5.83 Hz, 2H) 2.19 (s, 3H) 2.14 (s, 3H); MS 397.0 [M+1].

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue purified by prep chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a9e332bf9a8d4608b33031a699f60a92
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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