SU685156A3 - Method of obtaining n-(5-tetrazolyl)-1-oxo-1h-pyramido-(1,2-a)-quinolin-2-carboxamide - Google Patents

Description

(54) METHOD FOR PRODUCING N- (5-TETPA3O n) -l-OKCO-lH-pyrimido UA quinoline-2- carboxamide carbodiimides is used, for example, ditsiklogeksilkarbodiimvd, 1-cyclohexyl-Z- (2-morpholinomethyl) carbodiimide or 1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide chlorhydrate. Examples of solvents are N, N-dimethylformamide (DMF), tetrahydrofuran, dioxane, dyuroyurmethane, nitromethane or acetonitrile. The reaction of the acid with the condensing agent is carried out at 20-110 ° C. The intermediate compound then reacts with 5-aminotetrazole at 20 IO ° C. The molar ratio of acid: condensing agent: 5-aminotetrazole is usually 1: 1: 1 - 1: 1, 1: 1, 1. A satisfactory is 10 mol%. All reagents can be administered directly, and not in portions. However, with the preliminary formation of an intermediate, usually the yield of the desired M- (5-tetrazol-1) -amides increases. Example. M- (5-Tetrazolyl) -1-oxo-1H-6-methoxypyrimido-1,2-a} -quinoline-2-carboxamide. A mixture of 1-oxo-1H-6-methoxypyrm1iso-1,2-aJ-quinoline-2-carboxylic acid (540 mg, 2.0 mmol) and N, N -carbonyl-diimidazole (357 mg, 2.2 mmol) in DMF (15 ml) is stirred and heated on the steam bath for 14 minutes. After heating for about 5 minutes, the solution is clarified, and a precipitate is formed. The mixture is stirred for 45 minutes at room temperature, treated with 5-aminotetrazole (187 mg, 2.2 mmol), heated on the steam bath for 40 minutes, cooled and filtered to obtain 540 mg of a yellow solid, mp. 220 ° C (decomp.). The product is dissolved in hot DMF (200 mg of product per 20 ml of DMF, filtered. Hot solution, the filtrate is cooled, the yellow crystals are precipitated and dried, T.Sh1. (Dec.). Calculated,%: C 53.41 ; H 3.29; N 29.07 CisHjiN Os. Found: C 53.12; H 3.67; N 28.75. Similarly, compounds of the general formula 0 Vy Q -Jin- are obtained (Ij listed in Table 1 , and Table 2. Example 2. The products obtained as in Example 1 are converted to the salts of sodium, potassium, ammonium, calcium, magnesium and aluminum, triztypamine, tri-n-butylamine, piperidine, triethanolamine, daepshaminoethylamine, pyrrolidine and N, N-dibenzi ep lendiamina by reaction with an equivalent amount of metal hydroxide, ammonium hydroxide or amine in water or salt zhanole followed by filtration, if insoluble, or by evaporation of the solvent if the salt is soluble therein.

TABLE 2 Formula of the invention. Method for the preparation of N- {5-tetrazolyl) -1-oxo-pyrimido-1,2-a1-chshulin-2-carboxamide of the general formula RI where RI and R2 are hydrogen, Cj-Cs is alkyl, GI-GS - alkoxy group, fluorine or chlorine; B 6 - chlorine, bromine or Cj-Cs apkoxy group. characterized in that the acid of the general form where RI is Haz — as indicated above, is reacted with 5-aminotetrazole in an inert solvent at 20110 ° C in the presence of 1BY1 condensing areirra, such as, N-carbohydrate imidazole, N, N carbonyldi-5 -triazine, ztoxyacetylene, 1,1-DI (compound diethyl ether, D11-phenyl-4-a-3-a-3-ay-3, N-hydroxyphthalimide, N-hydroxypiperidine, ethylene chlorophosphite, diethylethylen pyrophosphite, Natsh1-5-phygasisoxazole 3-3 diesel carbamide or carbodimides, with the release of the target product. Sources 5shformshch1, p yn Tide into account in the examination 1. L F. Fieser, M. Fleser. Reagents oY organic Synthesis, New-Jerk-London-Sydney, Jonn .Wiley ond sons, Jnc, 1967, p. 114