UA125215U - 7-METHYL-2,4-DIOXO-3,7-DIAZAPYRO [BICYCLES [3.3.1] NONAN-9,1'-CYCLOHEXANE] -1,5-DICARBONITRIL - Google Patents

Abstract

7-Methyl-2,4-dioxo-3,7-diazaspiro [bicyclo [3.3.1] nonane-9,1'-cyclohexane] -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|Inonan | Soizepko M.M., KtgimoKoiuzKo 5.0., I ymipom 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 Hey, Ippy. Ed. 2007, 56, 2482 (Izv. AN. Ser. Chem. 2007, 2397);

Spidogipa E.A., EgoYom K.A., BoizepKo MM, soYomespKip A.5., VizPptagipom I.5., KgimoKoiuzKo 5.6.

Challenge Spent Howl, Ippy. Ed. 2016, 9, 2260 (Izv. AN. Ser. Chem. 2016, 2260); Spidogipa E.A., boyzepKo

M.M. Spent Neiegosusi Sotra. 2012, 48, 1722 (Heterocycle Chemistry. Joint 2012, 1838); GgoIbm

K.A., YuoizepKo MM, KtimoKoiuzKo 5.0., Iymipom M.R. Spent Self-employed. motherfucker 2012, 48, 442 (Chemistry of heterocyclic compounds 2012, 471); BoibvepKo M.M., EgoYom K.A., KhimokoiuzKo 5.0. 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); YuOoizepKo M.M., Egoiom K.A., KiimoKoiukheKo 5.0., SPidogipa E.A.,

ReKpiegema T.M., Bnukom 5.My., Rarauapipa E.5., YuOtishmepKo A.O., VybzPtagpom 1.5. Spent

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

A common essential feature of the analogues and the claimed utility model is that these compounds contain the basic structure 3,7-disabicyclo|3.3.1| nonan

The useful model, unlike its analogues, contains an oxygen atom in its composition instead of sulfur and selenium or a co-connected fragment in the case of its oxygen-containing analogues.

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

In accordance with this, a new compound is proposed in the useful model - 7-Methyl-2,4-dioxo-3,7-diazaspiro|bicyclo!|3.3.1| nonane-9,1"-cyclohexane|-1,5-dicarbonitrile (1).

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

SM

Mo

Mme-7 about nm is)

Zo 7-Methyl-2,4-dioxo-3,7-diazaspiro|(bicyclo13.3.1|nonane-9,1'-cyclohexane|-1,5-dicarbonitrile (I) (yield 26,950) is obtained as follows: to suspension of 2.16 mmol of 2,4-dioxo-3-azaspiro|(5.5)undecane-1,5-dicarbonitrile (|

Zupipezev5, IM, 463, 662 (Chopp UMieu 5 Zop5 1963); doip S UMyibop, Sgeispep 5. Mesogay,

Zaiiuapagauap A. bgipimzap, Pat. 56365311 4.32 mmol of methylamine and an excess (2.0 ml, 26.6 mmol) of 37 95% HCNO, free from impurities of paraform, were added to VII in 15-20 ml of ethanol. The mixture was boiled for 2 minutes with intense stirring, the resulting solution was filtered through a pleated paper filter. After cooling, the reaction mixture was acidified with 10 95% NOSI solution to pH 5-6. After 24 hours, the precipitate was filtered and washed with ethanol.

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

INs taken on the device "Magiap Opiyu Riiz (400 MHz)" in DMSO-dv--SSI" (1 71) (internal standard -

TMS). HPLC-MS analysis was performed on an "Adiepi 1100" liquid chromatograph with "PA" detectors, "EG5O Zedekh 75" combined with an "Adiepi I S/M5O MI" mass spectrometer, ionization - electrospray (E5-ARI). Elemental analysis was carried out on the device "RegKkeep-EIteg S, H,

M-Apaii2heg". Control of the individuality of the obtained compound was carried out by the TLC method on the plates of "5ishoi! ShM-254", 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. 7-Methyl-2,4-dioxo-3,7-diazaspiro|(bicycloΙ3.3.1|nonane-9,H-cyclohexane|-1,5-dicarbonitrile (1), white crystalline powder, m.p. 280-282 "S. NMR spectrum "H, 5, ppm: 1.46-1.50 m (2Н, СН»), 1.76-1.82 m (6Н, СНе), 2.03-2, 11 m (2Н, СН»), 2.28 s (ЗН, МОН»), 3.02 d (2Н, by 1Н SeН» and СН», / 1.8 Hu), 3.11 d (2Н, by 1Н СН» and С8Н» in 11.8 Hu), 12.43 s (1Н, МН). Mass spectrum, t/7: 287.2

IMANI, 285.2 |M-NO. Found, 9o: C 62.78; H 6.36; M 19.53. Si5NivMaO". Calculated, 90: C 62.92;

H 6.34; M 19.57.

Claims (1)

USEFUL MODEL FORMULA 7-Methyl-2,4-dioxo-3,7-diazaspiro(bicyclo/3.3.1|nonane-9,1'-cyclohexane|-1,5-dicarbonitrile: SM Mo Mme--773 c) NM is!