Oxalyl chloride → N-(6,7-Methylenedioxyquinolin4-yl)-N-[3-(N,N-dimethylamino)propyl]-2-iodo-4,5-dimethoxybenzamide

HRID 1942922Notes

Reaction equation

HRID 1942922 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6]([NH:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])=[CH:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2]1.C(Cl)(=O)[C:22](Cl)=[O:23].[I:27][C:28]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[C:29]=1C(O)=O>C(Cl)(Cl)Cl>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6]([N:14]([CH2:15][CH2:16][CH2:17][N:18]([CH3:19])[CH3:20])[C:22](=[O:23])[C:36]4[CH:35]=[C:34]([O:37][CH3:38])[C:33]([O:39][CH3:40])=[CH:29][C:28]=4[I:27])=[CH:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 106625572-Iodo-5,6-dimethoxybenzoic acidHCID 16112709N'-(6,7-Methylenedioxyquinolin-4-yl)-N,N-dimethylpropane-1,3-diamine

Product 1

HCID 22139496N-(6,7-Methylenedioxyquinolin4-yl)-N-[3-(N,N-dimethylamino)propyl]-2-iodo-4,5-dimethoxybenzamideYield 79%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared from N′-(6,7-Methylenedioxyquinolin-4-yl)-N,N-dimethylpropane-1,3-diamine (273 mg, 1.0 mmol), in 79% yield with a reaction time of 12 h, from the acid chloride prepared using 4.0 mmol of oxalyl chloride and 1.36 mmol of 2-iodo-5,6-dimethoxybenzoic acid. Compound 7e had: IR (CHCl3) 1650; 1H NMR (CDCl3) δ 1.93 (m, 1H), 2.16 (m, 1H), 2.34 (s, 6H), 2.58 (m, 1H), 3.31 (s, 3H), 3.47 (m, 1H), 3.75 (s, 3H), 3.95 (m, 1H), 4.55, (m, 1H), 6.16 (s, 1H), 6.39 (s, 1H), 7.04 (s, 1H), 7.28 (d, 1H, J=5.0), 7.31 (s, 1H), 7.38 (s, 1H), 8.56 (d, 1 h, J=5.0); 13C NMR (CDCl3) δ 25.8, 45.1, 47.2, 55.5, 56.1, 26.9, 82.7, 98.1, 102.3, 107.0, 110.1, 120.1, 121.5, 122.5, 133.5, 145.5, 148.1, 148.4, 148.6, 149.2, 149.7, 151.1, 170.1; HRMS calcd for C24H26IN3O5H, 564.0995; found 564.0990.

Workup

  1. customprepared
  2. custom1H NMR (CDCl3) δ 1.93 (m, 1H), 2.16 (m, 1H), 2.34 (s, 6H), 2.58 (m, 1H), 3.31 (s, 3H), 3.47 (m, 1H), 3.75 (s, 3H), 3.95 (m, 1H), 4.55, (m, 1H), 6.16 (s, 1H), 6.39 (s, 1H), 7.04 (s, 1H), 7.28 (d, 1H, J=5.0), 7.31 (s, 1H), 7.38 (s, 1H), 8.56 (d, 1 h, J=5.0)

Sources & evidence

ORD record
ord-9f28c1a36b7d4d8582b23654c91dca2e
Source dataset
uspto-grants-2013_03
Patent number
US08389721B2

Reaction notes

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