7-Methoxyisoquinolin-3-amine → 2-[(2-Bromo-pyridin-4-ylmethyl)-amino]-N-(7-methoxy-isoquinolin-3-yl)benzamide

HRID 600683Notes

Reaction equation

HRID 600683 reaction equation
CO[C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([Br:18])[CH:13]=1.[NH2:20][C:21]1[N:22]=[CH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[C:26]([O:31][CH3:32])[CH:25]=2>>[Br:18][C:14]1[CH:13]=[C:12]([CH2:11][NH:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:20][C:21]2[N:22]=[CH:23][C:24]3[C:29]([CH:30]=2)=[CH:28][CH:27]=[C:26]([O:31][CH3:32])[CH:25]=3)=[O:19])[CH:17]=[CH:16][N:15]=1

Participants

3

Reactant 2

HCID 233211627-Methoxyisoquinolin-3-amineHCID 58763671Methyl 2-{[(2-bromopyridin-4-yl)methyl]amino}benzoate

Product 1

HCID 231189782-[(2-Bromo-pyridin-4-ylmethyl)-amino]-N-(7-methoxy-isoquinolin-3-yl)benzamide

Procedure

2-[(2-Bromo-pyridin-4-ylmethyl)-amino]-N-(7-methoxy-isoquinolin-3-yl)benzamide was prepared from 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-benzoic acid methyl ester and 3-amino-7-methoxyisoquinoline in analogy to the procedures detailed in Example 4A; 1H-NMR (300 MHz, d6-DMSO) 10.62 (1H, s), 9.10 (1H, s), 8.51 (1H, s), 8.32 (1H, d), 8.11 (1H, t), 7.83-7.90 (2H, m), 7.60 (1H, s), 7.50 (1H, m), 7.38-7.41 (2H, m), 7.27 (1H, t), 6.66 (1H, t), 6.55 (1H, d), 4.54 (2H, d), 3.91 (3H, s).

Sources & evidence

ORD record
ord-ac0e3c0bf79f49d3bb40d099bdb80441
Source dataset
uspto-grants-2011_03
Patent number
US07902229B2

Reaction notes

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