4-tert-Butylbenzylamine → N-(4-tert-butylbenzyl)-2-(5-isoquinolinyl)propanamide

HRID 2056916Notes

Reaction equation

HRID 2056916 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[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>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:24](=[O:25])[CH:23]([C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:17]=2[CH:16]=[CH:15][N:14]=[CH:13]3)[CH3:27])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 27356554-tert-ButylbenzylamineHCID 120187082-(Isoquinolin-5-YL)acetic acidHCID 223376382-(Isoquinolin-5-yl)propanoic acid

Product 1

HCID 10247056N-(4-tert-butylbenzyl)-2-(5-isoquinolinyl)propanamide

Procedure

The title compound was prepared using the procedure described in Example 222B using 4-(tert-butyl)benzylamine and 2-(5-isoquinolinyl)propanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 347 (M+H)+; MS (ESI−) m/z 345 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.56 (d, J 7.1, 3H), 4.22 (d, J 6.1, 2H), 4.57 (q, J 7.1, 1H), 7.10 (d, J 8.5, 2H), 7.29 (d, J 8.5, 2H), 7.98 (t, J 7.5, 1H), 8.13 (d, J 7.1, 1H), 8.34 (d, J 7.8, 1H), 8.56 (d, J 6.8, 1H), 8.69 (m, 2H), 9.78 (s, 1H); Anal. Calcd for C23H26N2O+1.1 HCl:C, 71.46; H, 7.07; N, 7.25. Found: C, 71.13; H, 7.17; N, 7.02.

Sources & evidence

ORD record
ord-8e281ed8d2604648b3b3f56089725efd
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Reaction notes

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