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

HRID 2056936Notes

Reaction equation

HRID 2056936 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].[OH:13][CH:14]([C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][N:22]=[CH:23]2)[C:15](O)=[O:16].C1C2C(=C(CC(O)=O)C=CC=2)C=CN=1>CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:15](=[O:16])[CH:14]([OH:13])[C:18]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[CH:21][N:22]=[CH:23]3)=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 27356554-tert-ButylbenzylamineHCID 120187082-(Isoquinolin-5-YL)acetic acidHCID 223376972-Hydroxy-2-(isoquinolin-5-yl)acetic acid

Product 1

HCID 11291000N-(4-tert-butylbenzyl)-2-hydroxy-2-(5-isoquinolinyl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared using the procedure described in Example 222B using 4-(tert-butyl)benzylamine and hydroxy(5-isoquinolinyl)acetic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. [α]22D-47.2 (c 0.7, MeOH); MS (ESI+) m/z 349 (M+H)+; MS (ESI−) m/z 347 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.26 (s, 9H), 3.69 (s, 1H), 4.27 (d, J 6.1, 2H), 5.62 (s, 1H), 6.52 (br s, 1H), 7.17 (d, J 8.1, 2H), 7.29 (m, 3H), 7.67 (t, J 8.1, 1H), 7.82 (d, J 7.1, 1H), 8.10 (m, 2H), 8.44 (d, J 5.8, 1H), 8.71 (t, J 6.1, 1H), 9.30 (s, 1H); Anal. Calcd for C22H24N2O2+0.25 H2O: C, 74.87; H, 7.00; N, 7.94. Found: C, 75.22; H, 7.40; N, 7.80.

Sources & evidence

ORD record
ord-b35bd662451a4c94955f47f556c23b60
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Reaction notes

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