4-(Trifluoromethylthio)benzylamine → 2-(5-isoquinolinyl)-N-{4-[(trifluoromethyl)thio]benzyl}propanamide

HRID 586027

Reaktionsgleichung

Reaktionsgleichung von HRID 586027
[F:1][C:2]([F:13])([F:12])[S:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.[CH:14]1[C:23]2[C:18](=[C:19]([CH:24]([CH3:28])[C:25](O)=[O:26])[CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1.C1C2C(=C(CC(O)=O)C=CC=2)C=CN=1>>[CH:14]1[C:23]2[C:18](=[C:19]([CH:24]([CH3:28])[C:25]([NH:9][CH2:8][C:7]3[CH:10]=[CH:11][C:4]([S:3][C:2]([F:12])([F:1])[F:13])=[CH:5][CH:6]=3)=[O:26])[CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1

Komponenten

4

Edukt 3

HCID 27778754-(Trifluoromethylthio)benzylamineHCID 120187082-(Isoquinolin-5-YL)acetic acidHCID 223376382-(Isoquinolin-5-yl)propanoic acid

Produkt 1

HCID 100232722-(5-isoquinolinyl)-N-{4-[(trifluoromethyl)thio]benzyl}propanamide

Versuchsvorschrift

The title compound was prepared using the procedure described in Example 222B using 4-[(trifluoromethyl)thio]benzylamine and 2-(5-isoquinolinyl)propanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 391 (M+H)+; MS (ESI−) m/z 389 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.57 (d, J 7.1, 3H), 4.33 (d, J 6.1, 2H), 4.65 (q, J 7.1, 1H), 7.33 (d, J 8.1, 1H), 7.65 (m, 2H), 7.76 (m, 1H), 7.98 (m, 2H), 8.19 (d, J 7.1, 1H), 8.42 (d, J 7.8, 1H), 8.61 (br s, 1H), 8.62 (d, J 6.8, 1H), 8.73 (d, J 6.8, 1H), 8.96 (t, J 5.8, 1H), 9.86 (s, 1H); Anal. Calcd for C20H17F3N2OS+2.1 HCl: C, 51.44; H, 4.12. Found: C, 51.35; H, 3.91.

Quellen und Nachweise

ORD-Eintrag
ord-ff2aacc6511d47c086fb19e3769d636e
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933311B2

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