4-Amino-5-chloro-2-methoxybenzoic acid → 4-amino-5-chloro-N-[[4-(4-cyanobenzyl)-2-morpholinyl]methyl]-2-methoxybenzamide

HRID 1608191Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[CH2:4]1.[NH2:18][C:19]1[C:27]([Cl:28])=[CH:26][C:22]([C:23](O)=[O:24])=[C:21]([O:29][CH3:30])[CH:20]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[NH2:18][C:19]1[C:27]([Cl:28])=[CH:26][C:22]([C:23]([NH:1][CH2:2][CH:3]2[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=3)[CH2:4]2)=[O:24])=[C:21]([O:29][CH3:30])[CH:20]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-aminomethyl-4-(4-cyanobenzyl)morpholine (1.5 g) in dichloromethane (40 ml), 4-amino-5-chloro-2-methoxybenzoic acid (1.2 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.3 g) are added, and the resulting mixture is stirred at 25° C. for 3 hours. The reaction mixture is washed successively with water, aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure to give the title compound as an oil.

Workup

washThe reaction mixture is washed successively with water, aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record: ord-30d972dfa3644820a4982b54e0d25ab2
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04870074

Reaction notes

Loading…