Method of obtaining dialkylamides of 3-brome-1-adamantilalkancarbon acids

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention concerns chemistry of adamantane derivatives, namely to a new method of obtaining of dialkylamides of 3-brome-1-adamantilalkancarbon acids of the general formula:

R1,R2=H:R3=N(C2H5)2

R1, R2=CH3:R3=N(C2H5)2

which can be of interest as semiproducts in synthesis of some biologically active substances possessing antiviral activity. Method lies in interaction of 1,3-dehydroadamantane with dialkylamides of α-bromalkancarbon acids from the row: diethylamide of α-bromacetic acid, piperidide of α-brompropionic acid, diethylamide of α-bromo-isobutyric acid at mole ratio of reagents peer accordingly 1:3-4, in the environment of the initial dialkylamides of α-bromalkancarbon acids, at temperature of 80-90°C within 4-6 hours.

EFFECT: obtaining of bonds of declared structural formula, excluding reception stage adamantilealkanecarbon acids.

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The invention relates to the chemistry of adamantane derivatives, namely to a new way of getting dialkylamino 3-bromo-1-adamantanecarbonyl acids of General formula

R1,R2=H:R3=N(C2H5)2

R1, R2=CH3:R3=N(C2H5)2

which may be of interest as intermediates in the synthesis of some biologically active substances.

A method of obtaining bromine derivatives adamantylidene acids, in which the bromine atom is not in the 3rd position adamant-1-ilen fragment, as in α-position of the hydrocarbon side chain, which consists in the treatment of 1-adamantylamine acid with thionyl chloride and the interaction of the obtained acid chloride with bromine and subsequent hydrolysis of the acid chloride α-bromo-1-adamantylamine acid. It α-bromo-1-adamantylamine acid [A.S. 910605, SS 101/04. Publ. 07.03.82,]. The output of this product reaches 70%.

The disadvantage of this method is that it allows you to get only one derivative (α-bromo-1-adamantylamine acid), and this method does not lead to obtaining substances claimed structural formulas.

A method of obtaining α-amino-(substituted-1)-acetic acid who you and α -amino-(substituted-1)-propionic acid using α-bromo-1-adamantylamine acid and (substituted-1)-propionic acid. Similar to previous, after halogenation source halides J2(Br2and subsequent ammonolysis of a 19%solution of NH4OH in methyl alcohol produced products with the release of 75-85% [Synthesis, decomposition and chemical transformation α-amino acids adamantanol range / Krasutsky P.A., Novikova M.I., Semenov I.G. // Chemistry and technology of Organoelement intermediates and polymers; proc. Dokl. The scientific. Conf., Volgograd, 1984/Volpi - Volgograd, 1984. - S. 138-141].

This method does not lead to obtaining substances claimed structural formulas.

Know the use of (substituted-2)-acetic acid to obtain α-amino-(substituted-2)-acetic acid. From (substituted-2)-acetic acid get its ethyl ester, which is then bromilow, receiving α-bromo-(substituted-2)-acetic acid. The obtained bromo derivatives reacts with ammonia, resulting in α-amino-(substituted-2)-acetic acid [Hromadko Soja. α-Amino-2-adamantylessigsaure und verhafren zu your herstellung // Patent DE 2521895. - 1976].

This method does not lead to obtaining substances claimed structural formulas.

The method for obtaining the amides of 1-adamantylamine acid by the reaction of acid chloride of adamantyl ssnoi acid with ammonia, aniline or N-alkylamines followed by (N-methylamine) [Tadashi Sasaki, Shoji Eguchi, Toru Takeshi. Synthesis of adamantane derivatives from adamantylacetic acid / Bull. Chem. Soc. Japan, 1968, 41, No. 1, p 233-240 (eng.) Pat. U.S. No. 3352912, CL. 260-563, publ. 14.11.67].

This method also does not receive dialkylamino 3-bromo-1-adamantanecarbonyl acids.

Closest to the proposed invention is a method of synthesis of 3-bromo-1-adamantanecarbonyl [Stetter H., Mayer J. Chem. Ber. 1962, 95, 667] and 3-bromo-1-adamantylamine acid [Bott, K. Chem. Ber. 1968, 707, 564-573] by direct synthesized 1-adamantanecarbonyl or 1-adamantylamine acids in the presence or in the absence of a catalyst.

The disadvantage of this method is the limited number of synthesized compounds, so that in this way it is impossible to obtain the claimed compounds of structural formulas.

The task of the invention is to develop technological molestating synthesis method dialkylamino 3-bromo-1-adamantanecarbonyl acids that occur with high yield by source adamantane.

The technical result is the expansion of the range of chemical compounds, in particular the acquisition of new dialkylamino 3-bromo-1-adamantanecarbonyl acids at one stage with high output.

The technical result is achieved in a new way to get dialkylamino 3-bromo-1-adamantyl cancerbook acids of General formula

R1,R2=H:R3=N(C2H5)2

R1, R2=CH3:R3=N(C2H5)2

by reacting 1,3-dehydroalanine with dialkylamide α-bromocarbon acids of the series: diethylamid α-bromoxynil acid, piperidin α-bromopropionic acid, diethylamide α-promisable acid at a molar ratio of reagents, respectively 1:3-4, in the environment of the source dialkylamino α-bromo-alkenylboronic acid, at a temperature of 80-90°C for 4-6 hours.

R1,R2=H:R3=N(C2H5)2

R1, R2=CH3:R3=N(C2H5)2

The essence of the method is the reaction of obtaining dialkylamino 3-bromo-1-adamantanecarbonyl acids by the reaction of joining 1,3-dehydroalanine relevant dialkylamino α-bromocarbon acids.

The reaction is based on previously unknown properties of 1,3-dehydroalanine to interact liaison carbon-halogen bonds in dialkylamide α-bromocarbon acids. The reaction is unknown, as the literature contains no information about the interaction of 1,3-dehydroalanine with dialkylamides the α -bromocarbon acids or related compounds. Interaction is possible due to high mobility of the halogen in dialkylamide α-bromocarbon acids generated electron-acceptor effect located at the nearest methylene (retinovoy) the carboxyl group of the fragment. The high nucleophilicity of 1,3-dehydroalanine allows you to get the addition products in high yields in a fairly mild conditions.

The method is as follows.

The 3-4-fold molar excess of dialkylamide α-bromo-alkenylboronic acid is poured a solution of 1,3-dehydroalanine in boiling inert solvent (diethyl ether), which is then removed from the reaction mixture by distillation. A mixture of 1,3-dehydroalanine and dialkylamide α-bromo-alkenylboronic acid is heated for 4-6 hours at a temperature of 80-90°C, after which the excess of the original dialkylamide α-bromocarbon acid is distilled off. It is possible to regenerate the original dialkylamino α-bromocarbon acids by distillation from the reaction mixture and the organization of recycling with the addition of the calculated amount of fresh dialkylamide α-bromocarbon acid. Synthesized dialkylamide 3-bromo-1-adamantanecarbonyl acids purified by vacuum distillation. You are the odes of these products are 65-88%.

We have studied some regularities flow between 1,3-dehydroalanine with dialkylamide α-bromocarbon acids. As studies have shown, the most convenient condition for the reaction joining dialkylamino α-bromocarbon acid to 1,3-dehydroalanine is its implementation in an environment of excess of original dialkylamino α-bromocarbon acid at a molar ratio of 1,3-dehydroalanine: dialkylamide α-bromocarbon acid=1:3-4. Less excess has resulted in a slight decrease of the yield of the target products due to possible homopolymerization 1,3-dehydroalanine and incomplete conversion. Further increase in the content of dialkylamide α-bromocarbon acid did not affect the yield of target products was inappropriate. The optimal reaction temperature is 80-90°C. lowering the temperature to room leads to a strong increase in the duration of this interaction and the reduction of the yield of target products, while further increasing along with the acceleration of the reaction causes a slight darkening of the reaction mixture and the yield of the pure product. The optimal treatment duration is 4-6 hours. The reduction of the reaction time leads to incomplete conversion of 1,3-digidroid is Montana and reduce the yield of the target product. The increase in reaction time is impractical due to the full conversion of 1,3-dehydroalanine.

The structure of the synthesized compounds are confirmed by the H-NMR, mass spectroscopy and elemental analysis.

The invention is illustrated by the following examples

Example 1.

Diethylamide (3-bromo-1-substituted)acetic acid

To 17.1 g (0.088 mol) of diethylamide α-bromoxynil acid in dry nitrogen atmosphere at room temperature pin solution of 3 g (0.022 mol) svezheosazhdennoi 1,3-dehydroalanine (ratio of 1,3-DCA: diethylamid α-bromoxynil acid =1:4) in 20 ml of absolute diethyl ether, after which the solvent is distilled off, the reaction mixture was kept at a temperature of 80-85°C for 5 hours, after which the excess diethylamide α-bromoxynil acid is removed by distillation, the residue is distilled in vacuum and obtain 6.35 g (0.0194 mol) of diethylamide (3-bromo-1-substituted)acetic acid. Yield 88%. TKip.=238-239°C / 10 mm Hg NMR Spectrum1N, δ, ppm: 1.030, 1.106 2T (3+3H, 2CH3), [S (1H), s (3H), s (1H), s (1H), s (2N), s (2N), s (4H) (substituted-1,3)], s (2H, (CH2WITH), 3.199-3.270 kV (2H, (CH2)2N). Found, %: C 58.56, H 8.01, N 4.23. C16H26BrNO. Calculated, %: C 58.54, H 7.98, N 4.27.

Example 2.

Piperidyl 2-(3-bromo-1-substituted)propionic acid.

To 14.5 g (0.066 mol) of piperidine α-bromopropionic acid in dry nitrogen atmosphere at room temperature pin solution of 3 g (0.022 mol) svezheosazhdennoi 1,3-dehydroalanine (ratio of 1,3-DCA: ethyl ether α-bromopropionic acid=1:3) in 20 ml of absolute diethyl ether, after which the solvent is distilled off, the reaction mixture was kept at a temperature of 85-90°C for 4 hours, after which the excess of piperidine α-bromopropionic acid is removed by distillation, the residue is distilled in vacuum and receive 6.31 g (0.0178 mol) of piperidine 2-(3-bromo-1-substituted)propionic acid. Yield 81%. TKip.=235-238°C / 2 mm RT. senior Mass spectrum, m/z, I %: 353-355 (13%, [M]+), 274 (83%, [M-Br]+), 241 (3%, [BrAdCH=CH2]+), 215 (1%, [AdBr]+), 133-135 (22%, [Ad]+). An NMR spectrum1H δ, ppm: 0.92 t (3 H, CH3); 1.42-1.76 m, 2.10s, 2.21-3.34 3D (14N, 1,3-substituted+6N, (CH2)3), 2.65 kV (1H, SNA(O)), 3.43-3.54 2T (4H, -N(CH2)2). Found, %: C 61.05, H 7.95, N 4.00. C18H28BrNO. Calculated, %: C 61.02, H 7.97, N 3.95.

Example 3.

Diethylamid 2-methyl-2-(3-bromo-1-substituted)propionic acid.

To 14.65 g (0.066 mol) of diethylamide α-promisable acid in an atmosphere of dry nitrogen at room temperature was added dropwise a solution of 2 g (0.015 mol) svezheosazhdennoi 1,3-dehydroalanine (ratio of 1,3-DCA: diethyl-the MFA α -promisable acid=1:3) in 15 ml of absolute diethyl ether, after which the solvent is distilled off, the reaction mixture was kept at a temperature of 85-90°C for 6 hours, the excess diethylamide α-promisable acid is removed by distillation, the residue is distilled in vacuum and get 5.09 g (0.0143 mol) of diethylamide-2-methyl-2-(3-bromo-1-substituted)propionic acid. Yield 65%. TKip.=247-249°C / 10 mm Hg NMR Spectrum1N, δ, ppm: 1.03-1.196 t (6 H, 2CH3); 1.533, 1.604, 1.66, 1.927, 2.078, 2.193, 2.229, 2.535, 2.779 9c (14N, 1,3-substituted; 6N, 2CH3); 3.128-3.287 kV (4H, -N(CH2)2). Found, %: C 60.72, H 8.42, N 3.89. C18H30BrNO. Calculated, %: C 60.67, N 8.49, N, 3.93.

Conclusions

Developed a new one-step method to produce dialkylamino 3-bromo-1-adamantanecarbonyl acids to obtain the claimed compounds of structural formula with high yields. The structure of the obtained compounds was confirmed mass, NMR1N-spectroscopy and elemental analysis.

The method of producing dialkylamino 3-bromo-1-adamantanecarbonyl acids of General formula

R1,R2=H:R3=N(C2H5)2

R1,R2=CH3:R3=N(C2H5)2,

which consists in the interaction of 1,3-dehydro is amantani with dialkylamide α -bromocarbon acids of the series: diethylamid α-bromoxynil acid, piperidin α-bromopropionic acid, diethylamide α-promisable acid at a molar ratio of reagents, respectively 1:3-4, in the environment of the source dialkylamino α-bromocarbon acid, at a temperature of 80-90°C for 4-6 hours



 

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FIELD: medicine, pharmaceutics.

SUBSTANCE: invention concerns chemistry of adamantane derivatives, namely to a new method of obtaining of dialkylamides of 3-brome-1-adamantilalkancarbon acids of the general formula:

R1,R2=H:R3=N(C2H5)2

R1, R2=CH3:R3=N(C2H5)2

which can be of interest as semiproducts in synthesis of some biologically active substances possessing antiviral activity. Method lies in interaction of 1,3-dehydroadamantane with dialkylamides of α-bromalkancarbon acids from the row: diethylamide of α-bromacetic acid, piperidide of α-brompropionic acid, diethylamide of α-bromo-isobutyric acid at mole ratio of reagents peer accordingly 1:3-4, in the environment of the initial dialkylamides of α-bromalkancarbon acids, at temperature of 80-90°C within 4-6 hours.

EFFECT: obtaining of bonds of declared structural formula, excluding reception stage adamantilealkanecarbon acids.

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FIELD: chemistry.

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FIELD: chemistry.

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and method of obtaining from the latter of carbamate derivative of general formula (6) where X1 represents halogen atom and R1 represents acyl group selected from C1-C7-linear or branched aliphatic acyl group, C3-C6-cycloalkylcarbonyl group, and aromatic acyl group, R3 represents alkyl group. Methods include interaction of benzyl derivative of general formula (1)

with halogen compound of general formula (2): where X2 represents halogen atom, and R2 represents acyl group selected from C1-C7-linear or branched aliphatic acyl group, C3-C6-cycloalkylcarbonyl group, and aromatic acyl group, in presence of Lewis acid. From obtained compound of general formula (3) carbamate derivative of general formula (6) is obtained. For this purpose compound of general formula (3) is subjected to hydrolysis obtaining aminoderivative of general formula (4)

which is further subjected to interaction with ester of halogen-formic acid of general formula (5) where X1 and R2 are determined above, X3 represents halogen atom, and R3 represents alkyl group, in presence of base. Invention also relates to novel acylbenzylamine derivatives of general formula (7):

where X1 represents halogen atom, each of R2 and R4 independently represents C1-C7-linear or branched aliphatic acyl group, C3-C6-cycloalkylcarbonyl group, and R can additionally represent hydrogen atom. Benzylamine derivatives of formula (3) and formula (7) can be used as intermediate products for obtaining agricultural or garden bactericide based on formula (6) carbamate.

EFFECT: elaboration of improved method of obtaining benzylamine derivative.

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FIELD: chemistry.

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EFFECT: method enables to achieve high output (86-95%) of chlorine-substituted 4,41-diaminobenzanilides and minimise amount of wastes.

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FIELD: chemistry.

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EFFECT: compounds with monoaminooxidase B inhibition properties applicable in obtainment of pharmaceutical drugs with relevant effect.

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