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PROCESS FOR PREPARING A PYRROLECARBOXAMIDE COMPOUND

IP.com Disclosure Number: IPCOM000245805D
Publication Date: 2016-Apr-11
Document File: 3 page(s) / 34K

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PROCESS FOR PREPARING A PYRROLECARBOXAMIDE COMPOUND

[0001]          The present document discloses a process for preparing N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide, which is represented by Formula (I):

 (I).

[0002]          The present document discloses a process for preparing N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide (compound I), said process comprising:

a)       obtaining a solution comprising N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide in an organic solvent;

b)       extracting the bisulfite adduct of N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide into an aqueous phase; and

c)       hydrolyzing the bisulfite adduct of N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide.

[0003]          The solution comprising N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide can be obtained for example by reacting N,N-diethylethylenediamine with an activated derivative of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, such as for example the activated ester that is obtained by reacting 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid with a mixture of N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide and 1-hydroxybenzotriazole. Alternatively, the solution comprising N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide can also be obtained for example by dissolving N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide in a suitable organic solvent.

[0004]          The organic solvent can be selected from the list comprising anisole, benzene, 1-butanol, butyl acetate, tert-butylmethyl ether, carbon tetrachloride, chlorobenzene, chloroform, cumene, cyclohexane, cyclopentyl methyl ether, 1,2-dichloroethane, 1,1-dichloroethene, 1,2-dichloroethene, dichloromethane, 1,1-diethoxypropane, 1,2-dimethoxyethane, 1,1-dimethoxymethane, 2,2-dimethoxypropane, 1,4-dioxane, ethyl acetate, ethyl ether, ethyl formate, heptane, hexane, isobutyl acetate, isooctane, isopropyl acetate, isopropyl ether, methyl acetate, 3-methyl-1-butanol, methylbutyl ketone, methylcyclohexane, methyl ethyl ketone, methyl isobutyl ketone, methyl isopropyl ketone, 2-methyltetrahydrofuran, pentane, petroleum ether, propyl acetate, t...