UA125211U - 7- (1-METHYETHYL) -2,4-DIOXO-3,7-DIAZOSPIRO [BICYCLES [3.3.1] NONAN-9,1'-CYCLOHEXANE] -1,5-DICARBONITRIL - Google Patents

Abstract

7- (1-Methylethyl) -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 piperidine derivatives, which may find their application as compounds with directed pharmaceutical action or "building blocks" for obtaining new valuable organic compounds.

Aminomethylation products of imides are closest to the claimed compound

Guareski - derivatives of 3,7-diazabicyclo/3.3.1|Yinonan | Soizepko M.M., KtgimoKkoiuzKo 5.S2., 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);

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

Ex. 5 Spent Howl, Yippee. Ed. 2016, 9, 2260 (Izv. AN. Ser. Chem. 2016, 2260); Spidogipa E.A., Ooivzepko

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

Egoiom K.A., OoivepKo MM, KimoKkoiuvzKo 5.S1., | Pmipom M.R. Spent Self-employed. Sotra 2012, 48, 442 (Chemistry of heterocyclic compounds 2012, 471); OoizepKo M.U., EgoYiom K.A., KgimoKoiuzKo 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); YuOoibvepko M.M., Egoiom K.A., KhimokoiuzKo 5.0., SPidogipa B.A.,

ReKpiegema T.M., Byukom 5.My., Rarauapipa E.5., Yutiimiepko A.O., VyvPptagipom I.5. Set.

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 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.

A useful model task is to create a new piperidine derivative.

In accordance with this, a new compound is proposed in the useful model - 7-(1-methylethyl)-2,4-dioxo-3,7-diazaspiro(bicycloΙ3.3.1|nonane-9,1"-cyclohexane|-1,5-dicarbonitrile (1).

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

Mo

SM ate o nm o

Zo 7-(1-Methylethyl)-2,4-dioxo-3,7-diazaspiro|bicyclo|3.3.1|nonane-9,1"-cyclohexane|-1,5-dicarbonitrile (I) (yield 29 95) obtained as follows: to a suspension of 2.16 mmol of 2,4-dioxo-

Z-azaspiro|5.5)undecane-1,5-dicarbonitrile (I. Stsageb5spi I., Set. 2BI, 1901, 579 and Ogadapis

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

Zaiiuapagauap A. bgipimzap, Pat. О56365311 VI1| 4.32 mmol of isopropylamine and an excess (2.0 ml, 26.6 mmol) of 37956-HCNO, free from impurities of paraform, were added to 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 a 1095 solution of HCl 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 Opyu Rii (400 MHz)" in DMSO-yvkssi" (1:1) (internal standard - TMO). NMR spectra of "C" were recorded on the device "VgyKeg Amapse PI NO (100.6 MHz)" in DMSO-av.

IR spectra were obtained on an IKO-29, LOMO spectrophotometer in petroleum jelly. 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 plates "5iYishshhoYi I OOM-254", 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.

7-(1-Methylethyl)-2,4-dioxo-3,7-diazaspiro|bicyclo|3.3.1|nonan-9,1"-cyclohexane|-1,5-dicarbonitrile (I), white crystalline powder, t pl. 240-242 70. IR spectrum, o, cm": 3443, 3275 (М-Н), 2250, 2177 (2 С-М), 1714, 1693 (2 С-0). NMR spectrum "H, 5, ppm: 0.90 d (ЗН, СН(СН»З3)», U 6.6

Hu), 0.93 d (ЗН, СН(СНЗ)», at 6.6 Hz), 1.46-1.54 m (2Н, СНге), 1.77-1.81 m (4Н, СНе), 1.81-1.85 m (2Н,

СН»), 2.03-2.07 m (2Н, СНе), 2.80-2.90 m (1Н, СН(СНЗ)»), 3.00 d (2Н, each 1Н СеН» and С8Н», U 12.1 Hu), 3.32 d (2Н , by 1Н SeН and С8Н», at 12.1 HZ), 12.33 s (1Н, МН). NMR spectrum of "С, 5, ppm: 17.6, 20.0, 20.6, 24.0, 27.2, 33.0, 38.6 (С"' and С»), 49.2, 52.9 (С5 and С8), 116.8, 116.9 (2С- M), 167.3, 167.4 (2

S-O). Found, 90: C 64.89; H 7.06; M 17.80. С17Н22МаО". Calculated, 90: C 64.95; H 7.05; M 17.82. and

Claims (1)

FORMULA OF USEFUL MODEL 7-(1-Methylethyl)-2,4-dioxo-3,7-diazaspiro|bicyclo|3.3.1|nonane-9,1"-cyclohexane|-1,5-dicarbonitrile: Mo СМ иР о НИМ at.