Preparing 5-(4-(2-methyl-phenyl)-3-hydroxy-4H-(1,2,4)triazole-5-yl)-2,4-dihydroxy-methyl-butyl-benzamide, comprises reacting 2,4-dihydroxybenzaldehyde with halide compound and subsequently brominating, followed by oxidative cyclization

• Main Authors: KRIEGBAUM, EVA, RUTZ, MATTHIAS
• Format: Patent
• Language: English; German
• Published: 22.12.2011
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION ORPROCESSING OF GOODS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS; TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINSTCLIMATE CHANGE

Preparing 5-[4-(2-methyl-phenyl)-3-hydroxy-4H-[1,2,4]triazole-5-yl]-2,4-dihydroxy-methyl-butyl-benzamide (A1) and its salts, hydrates, alcoholates and tautomers, comprises: reacting 2,4-dihydroxybenzaldehyde (1a) with a halide compound (Q) and subsequently brominating; reacting the obtained benzaldehyde compound (2a) with 4-o-tolylsemicarbazide; reacting the obtained urea compound (3a) in an oxidative cyclization; reacting the obtained 1,2,4-triazole-3-ol compound (4a) with e.g. n-butylmethylamine to give triazolyl-N-methyl-benzamide compound (4b); and cleaving the protecting group. Preparing 5-[4-(2-methyl-phenyl)-3-hydroxy-4H-[1,2,4]triazole-5-yl]-2,4-dihydroxy-methyl-butyl-benzamide (A1) and its salts, hydrates, alcoholates and tautomers, comprises: (a) reacting 2,4-dihydroxybenzaldehyde (1a) with a halide compound of formula (R-X) (Q) and subsequently brominating or brominating (1a) and subsequently reacting with (II); (b) reacting the obtained benzaldehyde compound of formula (2a) with 4-o-tolylsemicarbazide; (c) reacting the obtained urea compound of formula (3a) in an oxidative cyclization to give 1,2,4-triazole-3-ol compound of formula (4a); (d) reacting (4a) with n-butylmethylamine and carbon monoxide to give triazolyl-N-methyl-benzamide compound of formula (4b); and (e) cleaving the protecting group R of (4b). R : benzyl, A, SiA3 or SiA2-Ar1; A : 1-6C alkyl; Ar1 : phenyl or 4-methoxyphenyl; and X : Br or Cl. An independent claim is included for 1-[(5-bromo-2,4-dibenzyloxy-phenyl)methyleneamino]-3-(o-tolyl)-urea (6a) and its salts. [Image] ACTIVITY : None given. MECHANISM OF ACTION : Heat shock protein 90 (HSP90) modulator. Verfahren zur Herstellung von 5-[4-(2-Methyl-phenyl)-3-hydroxy-4H-[1,2,4]triazol-5-yl]-2,4-dihydroxy-methyl-butyl-benzamid ("A1")sowie seiner Salze, Hydrate, Alkoholate und Tautomeren, dadurch gekennzeichnet, dass man a) i) 2,4-Dihydroxybenzaldehyd (1) mit einer Verbindung der Formel II R-XII,worin R Benzyl, A, SiA3 oder SiA2Ar, A Alkyl mit 1, 2, 3, 4, 5 oder 6 C-Atomen, Ar Phenyl oder 4-Methoxyphenyl, X Br, Cl oder bedeuten, umsetzt und anschließend bromiert oder ii) 2,4-Dihydroxybenzaldehyd (1) bromiert und anschließend mit einer Verbindung der Formel II umsetzt, b) den unter a) erhaltenen Benzaldehyd (2)worin R Benzyl, A, SiA3 oder SiA2Ar, A Alkyl mit 1, 2, 3, 4, 5 oder 6 C-Atomen, Ar Phenyl oder 4-Methoxyphenyl, bedeuten, mit 4-o-Tolylsemicarbazid umsetzt, c) den unter b) erhaltenen Harnstoff (3)worin R Benzyl, A, SiA3 oder SiA2Ar, A Alkyl mit 1, 2, 3, 4, 5 oder 6 C-Atomen,...