Diisopropylethylamine → 9-(Quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41554

Reaktionsgleichung

Reaktionsgleichung von HRID 41554
OC(C(F)(F)F)=O.[C:8]1(=[O:19])[C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12][CH2:11][CH2:10][NH:9]1.Cl[C:21]1[CH:30]=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C(O)C>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:29]=[CH:30][C:21]=1[N:16]1[CH2:17][CH2:18][C:13]2([C:8](=[O:19])[NH:9][CH2:10][CH2:11][CH2:12]2)[CH2:14][CH2:15]1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 2389382-ChloroquinoxalineHCID 468615352,9-Diazaspiro[5.5]undecan-1-one trifluoroacetate

Produkt 1

HCID 672517459-(Quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-oneAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

The mixture of 2,9-diazaspiro[5.5]undecan-1-one TFA salt ([1190586-22-1], 1.0 g, 3.5 mmol), 2-chloroquinoxaline ([1448-87-9], 0.77 g, 4.6 mmol), DIPEA (3.7 ml, 21 mmol) and DMAP (22 mg, 0.18 mmol) in ethanol (10 ml) was placed in a microwave tube. The tube was sealed and the suspension was heated at 160° C. for 2 h under microwave conditions. The mixture was filtered and the residue washed with ethanol. The filtrate was concentrated and the precipitate filtered and washed with ethanol. The combined solid material was dissolved in ethyl acetate, washed with water and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 0.81 g (77%) of the title compound as a pale yellow solid which was not further purified. [1H NMR (400 MHz, DMSO-d6) ♀ ppm 8.79 (s, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.53-7.58 (m, 2H), 7.31-7.39 (m, 2H), 4.22 (dt, J=13.5, 4.4 Hz, 2H), 3.37-3.49 (m, 2H), 3.06-3.15 (m, 2H), 1.91-2.05 (m, 2H), 1.75-1.83 (m, 2H), 1.65-1.75 (m, 2H), 1.44-1.55 (m, 2H); LCMS RtB=2.80 min, [M+H]+=297.2].

Aufarbeitung

  1. customwas placed in a microwave tube
  2. customThe tube was sealed
  3. filtrationThe mixture was filtered
  4. washthe residue washed with ethanol
  5. concentrationThe filtrate was concentrated
  6. filtrationthe precipitate filtered
  7. washwashed with ethanol
  8. dissolutionThe combined solid material was dissolved in ethyl acetate
  9. washwashed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2c3365bfdad04b4d927b0e6172fba61b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530648B2

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