UA125212U - 1'-benzyl-7-isopropyl-2,4-dioxo-1H, 5H-spiro [3,7-diazabicyclo [3.3.1] NONAN-9,4'-piperidine] -1,5-dicarbonitrile - Google Patents

Abstract

1'-Benzyl-7-isopropyl-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., KymoKoiuzKo 5. S., and Pmipom M. R.

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

M. M., KimoKoiuzKo 5. (i., I ymipom M. R. Mopaibvn!. Spet. 2007, 138, 489; RoizepKo U. U.,

KiimokoiuzKo 5. S., I ymipom MU. R. Viz55. Spent Howl, howl. Ed. 2007, 56, 2482 (Izv. AN Ser. chem. 2007, 2397); SPidogipa E. A., Ertoyom K. A., Yuoizepko M. M., Soiome5zNKip A. 5., VyvPptagipom I. 5.,

KimoKoiuzKo 5. (1. Vyb55. Spet. ViiYi, pi Ei. 2016, 9, 2260 (Izv. AN. Ser. khim. 2016, 2260);

SNidogipa E. A., YuoisepKo M. M. Spet. Self-employed. motherfucker 2012, 48, 1722 (Chemistry of heterocyclic compounds 2012, 1838); EgoYom K. A., YuOisepKo M. M., Ktimokoiu5Ko 5. (., I ymipom M. R. Spet.

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

Egoiom K. A., KhimokoiuzKo 5. p. Spent Self-employed. motherfucker 2013, 49, 657 (Chemistry of heterocyclic compounds 2013, 705); YuOivepko M. M., KimoKkoiu5Ko 5. S., I ymipom, M. R. Spet. Self-employed.

Sotra 2015, 51, 109 (Chemistry of heterocyclic compounds 2015, 51, 109); Ooizepko U. M., EgoYom K. A.,

KgiimoKoiuzKo 5. S., Spidogipa E. A., Rekniegema T. M., Zyukom 5. My., Rarauapipa E. 5., OtiiniepKo A.

O., VizPtagipom I. 5. Spet. Self-employed. motherfucker 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 a basic structure of 3,7-diazabicyclo/3.3.1|nonane.

The useful model, in contrast to the prototypes, contains an oxygen atom instead of sulfur and selenium or a conjugated 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-isopropyl-2,4-dioxo-1H, 5H-spiro|3,7-diazabicyclo/3.3.1|nonane-9,4-piperidine| -1,5-dicarbonitrile ().

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

M

RP

Mo

. SM i o o nm o i 1-Benzyl-7-isopropyl-2,4-dioxo-1H, / 5H-spiro|3,7-diazabicyclo|3.3.1|-nonane-9,4-piperidini-1,5 -dicarbonitrile (I) (yield 68 95) is obtained as follows: 2.2 mmol of isopropylamine and 26.6 mmol of 37 95 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 is added |Khy, U.; Hie, Y.; Nap, V.; Maupaga, Fr. 0.;

Spepaga, V. I.; eiaab, A. U. Raiiepi UUO2009097405| 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

IRs taken on the "Vhykeg OEH-500 (500 MHz)" device in DMSO-av (internal standard - TMS), NMR spectra of "ZS ART" were recorded on the "Magiap Opiku Riy5 (100.6 MHz)" device in SOSIz: DMSO-iv ( 211); IR spectra were obtained on an IKO-29, LOMO spectrophotometer in petroleum jelly. Mass spectra were recorded on an Adiepi 1100 liquid chromatograph with CAO, EG5O Zedekh 75 detectors, combined with an Adiepi GS/mass spectrometer M5O Mi", ionization - electrospray.

Elemental analysis was carried out on the device "RegKip-Eiteg S, H, M-Apaii2eg". Control of the individuality of the obtained compound was carried out by the TLC method on "ZiishShoYi ShM-254" plates, in the acetone-heptane system (1:11), 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. 1-Benzyl-7-isopropyl-2,4-dioxo-1H, 5H-spiro|3,7-diazabicyclo|3.3.1|nonane-9,4-piperidini-1,5-dicarbonitrile (I), white fine crystalline powder , t. pl. 228-230 "S. IR spectrum, m, cm": 3420, 3180 (MN), 2260 (С-М), 1730, 1713 (С-О). NMR spectrum "H, 5, ppm (U, Hz): 0.91 (6Н, d, 336.6, СН(СНЗ)2); 1.90-1.94 (2Н, m, СН»); 2.17-2.21 (2Н, m, CH"); 2.66-2.71 (2H, m, CH2g); 2.72-2.76 (2H, m, CH"); 2.84-2.89 (1H, m, CH(SnNZ3)g); 3.03 (2H, d, 290-11.5) and 3.25 (2Н, d, 29О-11.5, 6,8-СН»); 3.52 (2Н, s. s, СНеРИ); 7.23-7.29 (1Н, m, Н RI); 7.29-7.34 ( 4H, m, H RI); 12.43" (1H, s, MH). 7

The integrated intensity is reduced due to partial deuterium exchange. NMR spectrum "C ART, b, m.d.: 17.67 (CH(CHvz)g); 27.2; 32.9; 37.1; 47.5; 47.6; 49.3 (20); 52.7; 52.97 (CH(CHZ)2g); 61.6 ( SNeRY); 116.8 (S-M); 127.04 (0-4 RI); 128.27 (20. Ag); 128.67 (20. Ag); 138.0 (S-1 Ag); 167.1 (S-0). "Signals - in antiphase. Mass spectrum, t/2: 406 (MANI, 404.1 M-NI. Found, 90: C 68.25;

H 6.84; M 17.23. СгзНа?7М5О». Calculated, 95: C 68.13; H 6.71; M 17.27.

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

Claims (1)

USEFUL MODEL FORMULA 1-Benzyl-7-isopropyl-2,4-dioxo-1H,5H-spiro|3,7-diazabicycloY3.3.1|nonane-9,4-piperidine-1,5-dicarbonitrile: moss RP Mo. SM I-Rg nm o .