Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1999-06-10
2000-01-25
McKane, Joseph K.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
5483241, C07D23384, C07D40106
Patent
active
060180498
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for the preparation of carbamoylated imidazole derivatives.
BACKGROUND ART
Various imidazole derivatives have been researched to apply them to medicines, and they are assumed to be efficient as an antiviral agent or an anti-HIV agent.
It is described, as a process for the preparation of imidazole derivatives, that alcohol derivatives are reacted with 4,5-dicyanoimidazole, diethylazodicarboxylate, and triphenylphosphine (Tetrahedron Asymmetry. Vol. 5, No. 2, 181-184 (1994)). This process does not, however, include N-alkylation reaction of carbamoylated imidazole derivatives. It is described, as a process for the preparation of imidazole derivatives having a carbamoyl group at 2-position, that introduction of a carbamoyl group into 2-position of the imidazole ring is carried out after alkylation at 1-position (WO 96/10019). The reaction condition of the alkylation in this method is not mild.
DISCLOSURE OF INVENTION
The present inventors have intensively studied to develop, as a process for the preparation of carbamoylated imidazole derivatives, N-alkylation under mild condition without protection of the carbamoyl group, and succeeded in the reaction of imidazole derivatives of the following formula (I) with the compounds of the formula (II) in the presence of phosphine and either of dialkyl azodicarboxylate and tetraalkyl azodicarboxamide to give imidazole derivatives of the formula (III). Thus, the present invention has been accomplished.
Accordingly the present invention provides a process for the preparation of a compound of the formula (III): ##STR3## wherein R.sup.1 is an optionally substituted alkyl or an optionally substituted aryl; R.sup.2 is an optionally substituted alkyl; R.sup.3 is an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted aralkyl, or an optionally substituted heteroarylalkyl; and n is an integer of 1-3, ##STR4## wherein R.sup.1, R.sup.2, and n are as defined above, with a compound of the formula (II): either of dialkyl azodicarboxylate and tetraalkyl azodicarboxamide.
BEST MODE FOR CARRYING OUT THE INVENTION
Preferable embodiments of the present invention include the process wherein R.sup.3 OH is picolyl alcohol, the process wherein dialkyl azodicarboxylate is diisopropyl azodicarboxylate, and/or the process wherein phosphine is triphenylphosphine.
In the present specification, the term "alkyl" means a C1-C8 straight or branched chain alkyl, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl , t-butyl. n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, and the like. The alkyl may be substituted with halogen (fluoro, chloro, bromo, or iodo), aryl, cycloalkyl (e.g., cyclopropyl), and the like. One or more substituent(s) may be at any substitutable position(s).
The term "aryl" means a C6-C12 aromatic group, for example, phenyl, naphthyl, and the like. The aryl may be substitute with halogen, alkyl (e.g., methyl or ethyl), alkoxy (e.g., methoxy or ethoxy), nitro, and the like. One or more substituent(s) may be at any substitutable position(s). Examples of a substituted aryl include, for example, 3-fluorophenyl, 3-chlorophenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3-methylphenyl, 3,5-dimethylphenyl, 3-methoxyphenyl, 3,5-dimethoxyphenyl, 3-nitrophenyl, and the like.
The term "alkenyl" means a C2-C8 straight or branched alkenyl, for example, vinyl, allyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, and the like. The substituent on the alkenyl is the same as that on the above defined alkyl.
The term "aralkyl" means the above defined alkyl substituted with the above defined aryl, for example, benzyl, 1-phenylethyl, naphthylmethyl, 2-naphthylethyl, and the like. The substituent on the aralkyl is the same as that on the above defined aryl.
The term "heteroarylalkyl" means the above defined alkyl substituted with heteroaryl. The heteroaryl means a 5-6 membered cyclic group which contains one or more hetero atoms selected independently from the group consisting of oxygen,
REFERENCES:
patent: 5910506 (1999-06-01), Sugimoto et al.
CA 120: 271118p 5-Nitroimidazoles . . . thiols. Girard et al., p. 1148, 1994.
Hajima Makoto
Matsuda Koji
Takeuchi Yoshiyuki
McKane Joseph K.
Shionogi & Co. Ltd.
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