Benzenemethanamine, 3,5-dichloro- → N-(3,5-dichlorobenzyl)-2-(5-isoquinolinyl)propanamide

HRID 2056925Notes

Reaction equation

HRID 2056925 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5][NH2:6].[CH:11]1[C:20]2[C:15](=[C:16]([CH:21]([CH3:25])[C:22](O)=[O:23])[CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1.C1C2C(=C(CC(O)=O)C=CC=2)C=CN=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5][NH:6][C:22](=[O:23])[CH:21]([C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[CH:14]=[CH:13][N:12]=[CH:11]2)[CH3:25]

Participants

4

Reactant 3

HCID 457602Benzenemethanamine, 3,5-dichloro-HCID 120187082-(Isoquinolin-5-YL)acetic acidHCID 223376382-(Isoquinolin-5-yl)propanoic acid

Product 1

HCID 22032667N-(3,5-dichlorobenzyl)-2-(5-isoquinolinyl)propanamide

Procedure

The title compound was prepared using the procedure described in Example 222B using 3,5-dichlorobenzylamine 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), 4.20 (m, 2H), 4.53 (q, J 7.1, 1H), 7.13 (s, 2H), 7.42 (s, 1H), 7.78 (t, J 7.8, 1H), 7.89 (d, J 6.5, 1H), 8.17 (d, J 8.1, 1H), 8.23 (d, J 6.4, 1H), 8.59 (d, J 6.2, 1H), 8.64 (t, J 5.8, 1H), 9.51 (s, 1H).

Sources & evidence

ORD record
ord-3407f2b67035485dbca144c6ca3ed2b2
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Reaction notes

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