2-(Isoquinolin-5-YL)acetic acid → N-[4-(1-azepanyl)benzyl]-2-(5-isoquinolinyl)propanamide

HRID 887307Notes

Reaction equation

HRID 887307 reaction equation
[N:1]1([C:8]2[CH:15]=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:16]1[C:25]2[C:20](=[C:21]([CH:26]([CH3:30])[C:27](O)=[O:28])[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][N:17]=1.C1C2C(=C(CC(O)=O)C=CC=2)C=CN=1>>[N:1]1([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][NH:13][C:27](=[O:28])[CH:26]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]4[C:20]=3[CH:19]=[CH:18][N:17]=[CH:16]4)[CH3:30])=[CH:14][CH:15]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 120187082-(Isoquinolin-5-YL)acetic acidHCID 22337561[4-(Azepan-1-YL)phenyl]methanamineHCID 223376382-(Isoquinolin-5-yl)propanoic acid

Product 1

HCID 11749546N-[4-(1-azepanyl)benzyl]-2-(5-isoquinolinyl)propanamide

Procedure

The title compound was prepared using the procedure described in Example 222B using 4-(1-azepanyl)benzylamine and 2-(5-isoquinolinyl)propanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 388 (M+H)+; MS (ESI−) m/z 366 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.53 (m, 7H), 1.72 (m, 4H), 3.85 (s, 2H), 4.03 (q, J 7.1, 1H), 6.76 (m, 3H), 7.26 (m, 2H), 7.58 (m, 1H), 7.71 (m, 1H), 8.10 (m, 2H), 8.72 (t, J 5.8, 1H), 9.91 (s, 1H); Anal. Calcd for C25H29N3O+2.15HCl+2H2O: C, 59.82; H, 7.06. Found: C, 59.59; H, 7.28.

Sources & evidence

ORD record
ord-0619896780404a31b7120b7296edde51
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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