3-(Trifluoromethyl)benzylamine → 2-(5-isoquinolinyl)-N-[3-(trifluoromethyl)benzyl]propanamide

HRID 586026Notes

Reaction equation

HRID 586026 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].[CH:13]1[C:22]2[C:17](=[C:18]([CH:23]([CH3:27])[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]([CH3:27])[C:24]([NH:7][CH2:6][C:5]3[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=3)=[O:25])[CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 759623-(Trifluoromethyl)benzylamineHCID 120187082-(Isoquinolin-5-YL)acetic acidHCID 223376382-(Isoquinolin-5-yl)propanoic acid

Product 1

HCID 220326702-(5-isoquinolinyl)-N-[3-(trifluoromethyl)benzyl]propanamide

Procedure

The title compound was prepared using the procedure described in Example 222B using 3-(trifluoromethyl)benzylamine and 2-(5-isoquinolinyl)propanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 359 (M+H)+; MS (ESI−) m/z 357 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.54 (d, J 7.1, 3H), 4.28 (d, J 6.1, 2H), 4.50 (q, J 7.1, 1H), 7.41 (s, 1H), 7.49 (m, 2H), 7.56 (m, 1H), 7.80 (t, J 7.8, 1H), 7.95 (d, J 7.2, 1H), 8.21 (d, J 8.1, 1H), 8.32 (d, J 6.2, 1H), 8.60 (d, J 6.8, 1H), 8.72 (t, J 5.8, 1H), 9.56 (s, 1H).

Sources & evidence

ORD record
ord-f7d0ef2f3bf9417cb4fd1fb73d2fb2e3
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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