METHODS FOR PREPARING BIPHENYLISOXAZOLE SULFON- AMIDES

FIELD: organic chemistry, chemical technology. SUBSTANCE: invention relates to a novel method for preparing biphenylisoxazole sulfonamide of the formula (I) , its enantiomers and diastereomers and its salts where X means oxygen atom; Y means nitrogen atom; each of R3, R4 is bound with directly with...

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Hauptverfasser: VANG KSUEBAO, PANDIT CHENNAGIRI R, GADAMASETTI KUMAR G, DEPJU DZHEFFRI S, MARTINES EHDUARDO KH, POLNJAZHEK RICHARD P, PENDRI JADAGIRI
Format: Patent
Sprache:eng ; rus
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Zusammenfassung:FIELD: organic chemistry, chemical technology. SUBSTANCE: invention relates to a novel method for preparing biphenylisoxazole sulfonamide of the formula (I) , its enantiomers and diastereomers and its salts where X means oxygen atom; Y means nitrogen atom; each of R3, R4 is bound with directly with ring carbon and means independently alkyl; each of R1, R2 is bound directly with ring carbon and means independently hydrogen atom or alkyl; each of R11, R12, R13, R14 means independently hydrogen atom; J means oxygen atom; K means nitrogen atom; L means carbon atom; p = 0 or whole number from 1 to 2. Method involves: (a) interaction of pinacol ester of the formula (II) with halogenphenyl compound of the formula (III) in the presence of palladium (0) catalyst and, optionally, a base to yield nitrogen-protected derivative of the formula (IV) and (b) removal of protective group at nitrogen atom in compound of the formula (IV) to yield compound of the formula (I). Invention relates also to pinacol ester of the general formula (II) where X means oxygen atom; Y means nitrogen atom where each of R3, R4 is bound directly with ring carbon and means independently alkyl; each of R13, R14 is bound with ring carbon and means independently hydrogen atom; "prot" means nitrogen-protective group. Invention relates also to method for preparing compound of the formula (II) involving: (a) interaction of compound of the formula (V) with amine of the formula (VI) in the presence of organic base and organic solvent to yield compound of the formula (VII) ; (b) protection of nitrogen atom in indicated compound of the formula (VII) to yield compound of the formula (VIII) given in the invention claim; (c) preparing lithium derivative of indicated compound of the formula (VIII) using alkyl- or aryllithium compound and the following reaction of formed lithium derivative with trialkylborate and the following hydrolysis to yield boronic acid of the formula (IX) ; (d) interaction of indicated compound of the formula (IX) with pinacol, water removal to yield compound of the formula (II). Invention provides the novel method for preparing biphenylisoxazole sulfonamides. EFFECT: improved preparing method. 34 cl, 4 ex