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

HRID 2056935

Reaction equation

HRID 2056935 reaction equation
[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]([C:24]([CH3:29])([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.FC1C(F)=C(C(F)(F)F)C=CC=1CN>>[CH:14]1[C:23]2[C:18](=[C:19]([C:24]([CH3:29])([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

Participants

5

Reactant 4

HCID 27778754-(Trifluoromethylthio)benzylamineHCID 120187082-(Isoquinolin-5-YL)acetic acidHCID 223376132-(Isoquinolin-5-yl)-2-methylpropanoic acidHCID 223376172,3-Difluoro-4-(trifluoromethyl)benzenemethanamine

Product 1

HCID 220326622-(5-isoquinolinyl)-2-methyl-N-{4-[(trifluoromethyl)thio]benzyl}propanamide

Procedure

The title compound was prepared using the procedure described in Example 222B using 4-[(trifluoromethyl)thio]benzylamine and 2-(5-isoquinolinyl)-2-methylpropanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 405 (M+H)+; MS (ESI−) m/z 403 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.57 (s, 3H), 1.64 (s, 3H), 4.33 (d, J 6.1, 2H), 6.57 (s, 1H), 7.18 (m, 1H), 7.33(m, 1H), 7.52 (m, 2H), 7.82 (m, 1H), 8.11 (m, 1H), 8.36 (d, J 7.8, 1H), 8.57 (m, 1H), 9.42 (s, 1H), 10.08 (s, 1H); Anal. Calcd for C21H19F3N2OS+2 HCl: C, 52.84; H, 4.43. Found: C, 52.66; H, 4.39.

Sources & evidence

ORD record
ord-fb04c4b0e3524dc9890e5c4a298a716c
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Linked notes

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