UA126238U - 9-BUTYL-7,9-DIMETHYL-2,4-DIOXO-3,7-DIAZABicyclo [3.3.1] NONAN-1,5-DICARBONITRYL - Google Patents

Abstract

9-Butyl-7,9-dimethyl-2,4-dioxo-3,7-diazabicyclo [3.3.1] nonane-1,5-dicarbonitrile.

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|nonane (OoizepKo U. U., KiimoKoiuzKo 5. a., Iimipom U. R.

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

M. M., KimoKoiuzKo 5. (3., I ymipom M. R. Mopaibvn. Spet. 2007, 138, 489; RoyvepKo M. UM.,

KiimokoiuzKo 5. S., I ymipom M. R. Vyvv. Spent Howl! Yippie. Ed. 2007, 56, 2482 (Izv. AN. Ser. Chem. 2007, 2397); SNidogipa E. A., Egoiom K. A., BoisepKo U. U., SboiomevzNKip A. 5., VizPtagipom I. 5.,

KiimoKoiubzKo 5. S. NKyb55. Spent Yeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee Eh. 2016, 9, 2260 (Izv. AN. Ser. Chem. 2016, 2260);

Spidogipa E. A., OoibzepKo M. M. Spet. Self-employed. Sotra 2012, 48, 1722 (Chemistry of heterocyclic compounds 2012, 1838); Egoiom K. A., Yuoizepko U. M., KipimoKoiuzKo 5. S., I ymipom M. R. Snet.

Self-employed. motherfucker 2012, 48, 442 (Chemistry of heterocyclic compounds 2012, 471); JuoisepKo U.U.,

Egoiom K. A., KimoKoiuzKo 5. S. Spet. Self-employed. Sotra 2013, 49, 657 (Chemistry of heterocyclic compounds 2013, 705); Yuoivepko M. M., KimoKoiubKo 5. S., I Pmipom, M. R. Spet. Self-employed.

Sotra 2015, 51, 109 (Chemistry of heterocyclic compounds 2015, 51, 109); Royvepko U. U., Yegoyom K. A.,

KiiimoKoiuzKo 5. a., Spidogipa E. A., ReKpiegema T. M., Zytsukom 5. My., Rarauapipa E. 5., Otimiepko

A. O., VizPtaiipom I. 5. Spet. 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 (RAVSM, Bizriaipe).

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 -9-butyl-7,9-dimethyl-2,4-dioxo-3,7-diazabicyclo/3.3.1|nonane-1,5-dicarbonitrile (1) is proposed in a useful model.

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

Me

Mo Me

SM

Me o nm o a 9-Butyl-7,9-dimethyl-2,4-dioxo-3,7-diazabicycloY3.3.1|Inonane-1,-dicarbonitrile (I) (yield 67 95) is obtained as follows: mix the suspension 4 -butyl-4-methyl-3,5-dicyano-2,6-piperidindione (Guaresky imide) (Mogsgo55 M.V., MeiBagaev5 U.R., Boyega M.E., Zerpup M.A., Kiipeg S., 7akKnagom I.M., AzMNev R.S., Mapipeg 5.Yi., ViaKetoge R.V. U. Ogu. Spec. 2008, 73(20), 79391 (1.0 mmol) in 96 95 ethanol (20 ml), triethylamine (2-3 drops), methylamine (2.2 mmol) and 37 95 formaldehyde solution (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 pleated filter paper. After 12 hours, the mixture is acidified with hydrochloric acid to pH 6.0, kept at room temperature for hours, the precipitate is filtered off, washed with ethanol, the product is recrystallized from an acetone-ethanol mixture (1:1).

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

IN, taken on the device "Vhykeg OVH-500 (500/126 MHz)" in DMSO-iv (internal standard - TMSO),

IR spectra were obtained on an IKS-29, LOMO spectrophotometer in petroleum jelly. NRI S/M5 analysis was carried out on the "Adiyepi 1100" device with OAO and EI 50 bedeh 75 detectors, connected to

IIS/M50 Mi mass spectrometer and EB5BI system. Elemental analysis was carried out on the device "ReiKkip-EIteg S, H, M-Apaii2e!". Control of the individuality of the obtained compound was carried out by the TLC method on "5iiShsho! OM-254" plates, in the acetone-heptane system (1:1), development - iodine vapor, IR detector. The melting point was determined on a Kofler table and was uncorrected.

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.

9-Butyl-7,9-dimethyl-2,4-dioxo-3,7-diazabicycloY3.3.1|Inonane-1,5-dicarbonitrile (I), white fine crystalline powder, m.p. » 300 "C (decomposition); IR (KVh): 3326, 3195 (MH), 2250 (SEM), 1725, 1713 (S-O) cm"; NMR "H (500 MHz, DMS O-av): b 0.86 (t, ЗН, 39-7.1, СНеСН»), 1.23- 1.31 (m, 2Н, СНЕСНоСН), 1.45 (s, ЗН, СН), 1.48- 1.54 (m, 2H, SNСН»СНоСнН»), 1.63-1.66 (m, 2Н,

СНСНСНСН»), 2.27 (c, ЗН, МОН»), 3.04 (d, 2Н, 20-11.8, Н-6, Н-8), 3.07 (d, 2Н, 290-11.8, Н-6, Н-8 ), 12.36 (c, IN, MN); M5 t/ (Fe) 289.0 IM-A1T1", 287.1 |M-17. Calculated for Si5NgoMaO": C, 62.48; H, 6.99; M, 19.43. M - 288.35. Found: C, 62.44; H, 7.02; M , 19.40.

Thus, 9-butyl-7,9-dimethyl-2,4-dioxo-3,7-diazabicyclo-(3.3.1|nonane-1,5-dicarbonitrile (I) differs significantly from compounds of comparison.

Claims (1)

FORMULA OF USEFUL MODEL 9-Butyl-7,9-dimethyl-2,4-dioxo-3,7-diazabicycloY3.3.1|nonane-1,5-dicarbonitrile Me Mo Me SM Me NM o .