UA125207U - 7,9,9-TRIMETHYL-2,4-DIOXO-3,7-DIAZABicyclo [3.3.1] NONAN-1,5-DICARBONITRIL - Google Patents

Abstract

7,9,9-Trimethyl-2,4-dioxo-3,7-diazabicyclo [3.3.1] nonane-1,5-dicarbonitrile EMBED ISISServer.

Description

A useful model belongs to the field of organic synthesis, namely to new derivatives of piperidine, which may find their application as compounds with directed pharmaceutical action or "building blocks" for obtaining new valuable organic compounds.

The products of aminomethylation of imides are closest to the claimed compound

Guareski - derivatives of 3,7-diazabicyclo/3.3.1|Yinonan |Ooizepko M.M., KtgimoKoiuzKo 5.0., Iimipom M.R.

Spent Self-employed. Sotra 2005, 41, 1428 (Chemistry of heterocyclic compounds 2005, 1695); Ooivepko

M.M., KimoKoiuzKo 5.2., I ymipom M.R. Mopaibn. Spent 2007, 138, 489; Boyivepko MU.U., KipimoKoiuzko 5.0., I ymipom M.R. Ex. 5 Spent ViiYi., Ipi. Ed. 2007, 56, 2482 (Izv. AN Ser. chem. 2007, 2397);

SNidogipa E.A., EGgoYom K.A., YuoizepKo MU.U., SoYomevnKip A.5., Vybptagipom 1I.5., KimoKoiuzKo 5.0.

Ex. 5 Spent Vii., Ipi. Ed. 2016, 9, 2260 (Izv. AI. Ser. Chem. 2016, 2260); Spidogipa E.A., OoizepKo

M.M. Spent Self-employed. motherfucker 2012, 48, 1722 (Chemistry of heterocyclic compounds 2012, 1838);

Egoiom K.A., OoivepKo MM, KiimoKoiuvzKo 5.S1., and Pmipom M.R. Spent Self-employed. Sotra 2012, 48, 442 (Chemistry of heterocyclic compounds 2012, 471); OoizepKo M.U., EgoYiom K.A., KimoKoiuzKo 5.2. Spent

Self-employed. motherfucker 2013, 49, 657 (Chemistry of heterocyclic compounds 2013, 705); YuBoisepKo M.M.,

KimoKoiubzKo 5.2., I ymipom, M.R. Spent Self-employed. motherfucker 2015, 51, 109 (Chemistry of heterocyclic compounds 2015, 51, 109); YuoibhepKo M.M., Egoiom K.A., KimoKoiuzKo 5.0., Spidogipa E.A.,

ReKpiegema T.M., Btsukom 5.My., Rarauapipa E.5., YuOtimepKo A.O., VyvzPtagpom 1.5. Spent

Self-employed. Sotra 2016, 52, 116 (Chemistry of heterocyclic compounds 2016, 52, 116)).

A common essential feature of the prototypes and the claimed utility model is that these compounds contain the basic structure of 3,7-diazabicyclo|3.3.1|nonane (SAVSM, brizridipe).

The useful model, unlike the prototypes, contains an oxygen atom in its composition instead of sulfur and selenium, which lacks aryl or spiro-connected fragments in the case of comparison with oxygen-containing analogues.

The task of a useful model is to create a new derivative of piperidine.

Accordingly, a new compound - 7,9,9-trimethyl-2,4-dioxo-3,7-diazabicyclo|3.3.1|nonane-1,5-dicarbonitrile (1) is proposed in the useful model.

Compound I and methods of obtaining it are not described in patent publications.

Me

Mo Me

SM

Me o nm (in) .

Koo) 7,9,9-Trimethyl-2,4-dioxo-3,7-diazabicyclo/|3.3.1|nonane-1,5-dicarbonitrile (I) (yield 39 95) is obtained as follows: mix suspension 4, 4-dimethyl-3,5-dicyano-2,6-piperidindione (Guareschi imide) 126;

Napaieu S.9., Meizop E.V., Botegz T.O. A!yvig. ). Spet., 1960, 13, 129) (1.0 mmol) in 96 95 ethanol (20 ml), triethylamine (2-3 drops), methylamine (2.2 mmol) and 37905 solution of formaldehyde (formalin) (2.0 ml, 26.6 mmol). The mixture is stirred for 1 minute, boiled for 2 minutes, the resulting solution is filtered through a paper pleated filter. After 12 hours, the mixture is acidified with hydrochloric acid to pH 6.0, kept at room temperature for 6 hours, the precipitate is filtered, washed with ethanol, the product is recrystallized from a mixture of acetone-ethanol (1:1).

The structure of the compound obtained as a result of the reaction is confirmed by NMR spectra

IRs recorded on the "VgyKeg Amapse PI NO (400 МН2)" device in DMSO-4v (internal standard - TMS), NMR spectra of "ZS" were recorded on the "Magiap Opyu Riikh (100.6 MHz)" device in DMSO-dv; IR spectra were obtained on the IKOS-29, LOMO spectrophotometer in petroleum jelly. The elemental analysis was carried out on the Regkip-EIteg C, H, M-Apaii2eg device. The control of the individuality of the obtained compound was carried out by the TLC method on the plates "Zisho! OM-254", in the acetone-heptane system (1:1), development - iodine vapor, IR detector. The melting point was determined on a Kofler table and was not corrected.

The resulting product has sufficient purity for analysis and for further use.

A useful model is confirmed by the following example, which illustrates, but does not limit its scope.

Example. 7,9,9-Trimethyl-2,4-dioxo-3,7-diazabicyclo/3.3.1|Inonane-1,5-dicarbonitrile (I), white fine crystalline powder, m.p. 298-300 "C; IR spectrum, in (cm"): 3391, 3185 (MH), 2253 (SEM), 1740, 1725 (C-0); "H NMR, 5 (ppm): 1.33 (s, ZN, CH), 1.41 (s, ZN, CH), 2.28 (s, ZN, MON"), 3.03 (d, 2H, 211.7, H- 6, H-8), 3.10 (d, 2H, 290-11.7, H-6, H-8), 12.39 (sh. s, 1H, MN); "ZS NMR, 5 (m.d.): 19.3 (Me), 23.7 (Me), 36.9 (C-9), 42.9 (0-1, 0-5), 52.5 (MMe), 53.7 (C-6, 0-8), 115.0 (2 SEM), 167.0 (2

S-O). Calculated for С1и2НиаМаО»: С, 58.53; H, 5.73; M, 22.75. M-246.27. Found: C, 58.66; N, 5.87; M, 22.68.

Thus, 7,9,9-trimethyl-2,4-dioxo-3,7-diazabicyclo|3.3.1|nonane-1,5-dicarbonitrile (I) differs significantly from the comparison compounds in terms of structural and physicochemical properties.

Claims (1)

USEFUL MODEL FORMULA 7,9,9-Trimethyl-2,4-dioxo-3,7-diazabicyclo/3.3.1|Inonane-1,5-dicarbonitrile Me Mo Me SM Me we c)