4-(Trifluoromethyl)benzylamine → 2-(5-isoquinolinyl)-N-[4-(trifluoromethyl)benzyl]butanamide

HRID 586042

Reaction equation

HRID 586042 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH:13]1[C:22]2[C:17](=[C:18]([CH:23]([CH2:27][CH3:28])[C:24](O)=[O:25])[CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1.C1C2C(=C(CC(O)=O)C=CC=2)C=CN=1>>[CH:13]1[C:22]2[C:17](=[C:18]([CH:23]([CH2:27][CH3:28])[C:24]([NH:8][CH2:7][C:6]3[CH:9]=[CH:10][C:3]([C:2]([F:11])([F:12])[F:1])=[CH:4][CH:5]=3)=[O:25])[CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 768044-(Trifluoromethyl)benzylamineHCID 120187082-(Isoquinolin-5-YL)acetic acidHCID 223376822-(Isoquinolin-5-yl)butanoic acid

Product 1

HCID 220326662-(5-isoquinolinyl)-N-[4-(trifluoromethyl)benzyl]butanamide

Procedure

The title compound was prepared using the procedure described in Example 222B using 4-(trifluoromethyl)benzylamine and 2-(5-isoquinolinyl)butanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 391 (M+H)+; MS (ESI−) m/z 371 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 0.91 (t, J 7.5, 3H), 1.91 (m, 1H), 2.19 (m, 1H), 4.38 (m, 2H), 7.38 (d, J 8.5, 2H), 7.64 (d, J 8.5, 2H), 7.96 (t, J 7.8, 1H), 8.20 (d, J 7.1, 1H), 8.39 (d, J 8.1, 1H), 8.72 (s, 1H), 9.02 (t, J 6.8, 1H), 9.81 (s, 1H), 10.12 (br s, 1H); Anal. Calcd for C21H19F3N2O: C, 67.73; H, 5.14; N, 7.52. Found: C, 67.46; H, 4.90; N, 7.90.

Sources & evidence

ORD record
ord-9ef7d31270984120a61cef4cad579bea
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Linked notes

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