4-Hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents
A compound and alkyl technology, which can be applied to antiviral agents, compounds of group 4/14 elements of the periodic table, phosphorus organic compounds, etc., can solve the problems of no references, etc.
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[0180] Figures A-V The preparation of compounds of the invention is described. All starting materials were prepared by methods described in these figures or by methods analogous thereto, which are well known to those of ordinary skill in the art of organic chemistry. All final compounds of the invention are prepared by methods described in these figures or by methods analogous thereto, which are well known to those of ordinary skill in the art of organic chemistry. All variables used in the figures are as defined below or in the claims.
[0181] exist Figure A Among them, the compounds of the invention can be prepared by one of several methods starting from the appropriate 4-hydroxyquinoline-3-carboxylate a-1. In the first method A-1, ester a-1 is suspended in 5-10 parts of amine and the mixture is heated to 190-200° C. for 30 minutes to 4 hours. Product a-2 was isolated by diluting the cooled reaction mixture with hexane or toluene and collecting the solid precipitate b...
Embodiment 2
[0632] Elemental analysis found values: C, 56.74; H, 3.44; N, 7.35; Cl, 9.04. Example 2 7-amino-N-[(4-chlorophenyl)methyl]-4-hydroxyl-3-quinoline carboxamide
[0633] A suspension of 0.60 mL of 4-chlorobenzylamine and 0.200 g of ethyl 4-hydroxy-7-nitro-3-quinolinecarboxylate was heated at 180° C. for 1 hour. The reaction solution was cooled to room temperature. Ethyl acetate was added and the solid formed was collected and washed with ethyl acetate to give 0.071 g of the title compound as a tan solid.
[0634] The physical properties are as follows:
[0635] Mp 244-245°C (decomposition).
[0636] 1 H NMR (DMSO) δ 12.10, 10.63, 8.44, 7.85, 7.37, 7.31, 6.67, 6.53, 6.13, 4.49.
[0637] 13 C NMR (DMSO) δ 175.9, 165.6, 153.4, 142.8, 141.9, 139.3, 131.8, 129.6, 128.8, 127.1, 116.9, 114.8, 109.8, 97.9, 41.7.
[0638] IR (grinding) 3480, 3357, 2748, 2726, 1650, 1586, 1553, 1528, 1506, 1494, 1480, 1281, 789, 737, 621cm -1 .
[0639] MS(EI) m / z 327(M + ), 329, 327, 188, 18...
Embodiment 3
[0640] HRMS (EI) found 327.0778. Example 3 N-[(4-chlorophenyl)methyl]-8-fluoro-4,6-dihydroxy-3-quinoline carboxamide
[0641] To a mixture of 10% Pd / C and 2.0 g 3-fluoro-4-nitrophenol in 10 mL tetrahydrofuran and 10 mL methanol was added 4.817 g ammonium formate. After the reaction solution was stirred at room temperature for 1 hour, it was filtered through celite and then concentrated. Then 2.57 mL of diethyl ethoxymethylene malonate and 10 mL of xylene were added to the residue. The mixture was heated to 135°C for 1 hour and the ethanol formed was removed using a Dean-Stark trap. The reaction solution was cooled. The solid formed was collected, washed with hexanes and dried. The solid was then dissolved in 50 mL of diphenyl ether and heated to 250°C for 3 hours, collecting the ethanol with a Dean-Stark trap. The solution was cooled and diluted with hexanes. The solid formed was collected and dried to yield 0.527g. A solution of 0.415 g of this solid in 4 mL of 4-chl...
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