UA125221U - 1'-BENZYL-7- (2-METHYLPROPYL) -2,4-DIOXO-1H, 5H-SPYRO [3,7-DIAZABICYCLO [3.3.1] NONAN-9,4'-PIPERIDINE] -1,5-DICARBONITRIL - Google Patents

Abstract

1'-Benzyl-7- (2-methylpropyl) -2,4-dioxo-1H, 5H-spiro [3,7-diazabicyclo [3.3.1] nonane-9,4'-piperidine] -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|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. (1., I ymipom M. R. Mopaibvn. Spet. 2007, 138, 489; RoyvepKo M. UM.,

KiimokoiuzKo 5. S., I ymipom M. R. Vyv5. 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., YuOoizepko M. M. Spet. Neiegosusi Sotra. 2012, 48, 1722 (Chemistry of heterocyclic compounds 2012, 1838); Egoiom K. A., Yuoizepko U. M., KipimoKoiuzKo 5. S., I ymipom M. R. Snet.

Neiegosusi Sotra. 2012, 48, 442 (Chemistry of heterocyclic compounds 2012, 471); RoizepKko 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 analogs and the claimed utility model is that these compounds contain a basic structure of 3,7-diazabicyclo|3.3.1|Inonane.

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 - 1'"-benzyl-7-(2-methylpropyl)-2,4-dioxo-1H,5H-spiro|3,7-diazabicycloi|3.3.1|-nonane -9,4"-piperidine|-1,5-dicarbonitrile (1).

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

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Zo 1-Benzyl-7-(2-methylpropyl)-2,4-dioxo-1H,5H-spiro|3,7-diazabicyclo-3.3.1|nonane-9,4"- piperidine-1,5-dicarbonitrile ( I) (yield 40 95) is obtained as follows: 2.2 mmol of isobutylamine and 26.6 mmol of 37 96 formalin are added to 20 ml of 96 95 ethanol. The solution is stirred at room temperature for 1 hour, 1 mmol of 9- benzyl-2,4-dioxo-3,9-diazaspiro(5.5)undecane-1,5-dicarbonitrile (Khi, M.; Hie, Y.; Nap, V.; Maupaga, ah. 0.;

Spepaga, V. I; eiaar, A. 9). Raiepi MMO 2009097405)| and 2-3 drops of triethylamine, boil the resulting mixture for 2 minutes and quickly filter through a pleated paper filter.

After 12 hours, excess hydrochloric acid is added dropwise to pH 6. The resulting precipitate is filtered off and washed with ethanol.

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

IR spectra taken on the "Vhykeg OV8X-500 (500 MHz)" device in DMSOSO-av (internal standard - TMS) were obtained on the "IKOS-29, LOMO" spectrophotometer in petroleum jelly. Mass spectra were recorded on an Adiepi 1100 liquid chromatograph with OAO, EII5O bBedekh 75 detectors, combined with an Adiepi I S/M5O MI mass spectrometer, ionization - electrospray.

Elemental analysis was carried out on the device "ReiKip-EIteg S, H, M-Apaii2e!". Control of the individuality of the obtained compound was carried out by the TLC method on the "white SHM-254" plates, in the acetone-heptane (1 : 1) system, developed by 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.

1-Benzyl-7-(2-methylpropyl)-2,4-dioxo-1H,5H-spiro|3,7-diazabicyclo-3.3.1|nonane-9,4"- piperidine|-1,5-dicarbonitrile ( I), white fine crystalline powder, m.p. 210-212 "S. IR spectrum, y, cm": 3420, 3180 (MH), 2260 (S-M), 1737, 1710 (0-0). NMR spectrum "H, 5, ppm (U, Hz): 0, 71 (6Н, d, 33) - 6.6, СН(СНЗ3)»); 1.65-1.72 (1Н, m, СН(СНЗ)»); 1.92-1.96 (2H, m, CH); 2.17-2.21 (2H, m, CH); 2.21-2.25 (2H, m, СНеСН(СНЗ)»g); 2.67-2.71 (2H, m, CH); 2.72-2.76 (2H, m, CH); 3.03 (2H, d, 20-11.8) and 3.15 (2H, d, 29- 11.8, 6,8-CH»e); 3.53 (2H, w. s, SNeRY); 7.24-7.26 (1H, m, H RI); 7.28-7.34 (AN, m, H RP); 12.527 (1Н, с, МН). x Integral intensity reduced due to partial deuterium exchange.

Mass spectrum, t/2: 420.1 IMANI, 418.0 IM-NI. Found because: С 68,63; H 6.98; M 16.63.

SgaNgoM5O". Calculated, 90: C 68.71; H 6.97; M 16.69.

Thus, 1-benzyl-7-(2-methylpropyl)-2,4-dioxo-1H,5H-spiro|3,7-diazabicyclo/3.3.1|nonane-9,4"-piperidine|-1,5 -dicarbonitrile (I) is significantly different from the comparison compounds in terms of structural and physicochemical properties.

Claims (1)

USEFUL MODEL FORMULA 1-Benzyl-7-(2-methylpropyl)-2,4-dioxo-1H,5H-spiro|3,7-diazabicyclo/3.3.1|nonane-9,4-piperidine|- 1,5- dicarbonitrile: and RP Mo. SM shi o nm (in)