4-Bromobenzylamine → N-(4-bromobenzyl)-2-(5-isoquinolinyl)butanamide

HRID 2056930Notes

Reaction equation

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

Participants

Reactant 3

HCID 775714-Bromobenzylamine

HCID 120187082-(Isoquinolin-5-YL)acetic acid

HCID 223376822-(Isoquinolin-5-yl)butanoic acid

Product 1

HCID 22032640N-(4-bromobenzyl)-2-(5-isoquinolinyl)butanamide

Procedure

The title compound was prepared using the procedure described in Example 222B using 4-bromobenzylamine and 2-(5-isoquinolinyl)butanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 385, 383 (M+H)+; MS (ESI−) m/z 383, 381 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 0.91 (t, J 7.5, 3H), 1.81 (m, 1H), 2.19 (m, 1H), 3.39 (m, 1H), 4.22 (m, 2H), 7.13 (d, J 8.5, 2H), 7.44 (m, 3H), 7.57 (t, J 7.8, 1H), 8.00 (m, 1H), 8.21 (d, J 7.1, 1H), 8.41 (d, J 8.1, 1H), 8.72 (s, 1H), 8.93 (t, J 6.8, 1H), 9.81 (s, 1H), 10.16 (br s, 1H); Anal. Calcd for C20H19BrN2O: C, 62.67; H, 5.00. Found: C, 62.52; H, 4.95.

Sources & evidence

ORD record: ord-929d4571a7d545da9e5a206e8095ab95
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335678B2

Reaction notes

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