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

HRID 41554

Reaction equation

HRID 41554 reaction equation
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

Participants

6

Reactant 3

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

Product 1

HCID 672517459-(Quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-oneYield 78.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-2c3365bfdad04b4d927b0e6172fba61b
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Linked notes

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