Water → HCID 53259467, compound

HRID 41555Notes

Reaction equation

HRID 41555 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[N:11]1[CH2:22][CH2:21][C:14]2([C:19](=[O:20])[NH:18][CH2:17][CH2:16][CH2:15]2)[CH2:13][CH2:12]1.[H-].[Na+].Br[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[O:37][N:36]=[C:35]([CH3:38])[N:34]=1.O>CCCC[N+](CCCC)(CCCC)CCCC.[I-].C1COCC1.C(OCC)(=O)C>[CH3:38][C:35]1[N:34]=[C:33]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH2:26][N:18]2[CH2:17][CH2:16][CH2:15][C:14]3([CH2:21][CH2:22][N:11]([C:2]4[CH:3]=[N:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=4)[CH2:12][CH2:13]3)[C:19]2=[O:20])[O:37][N:36]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 242295035-[2-(Bromomethyl)phenyl]-3-methyl-1,2,4-oxadiazoleHCID 672517459-(Quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

Product 1

HCID 53259467HCID 53259467, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one (41 mg, 0.14 mmol) and TBAI (2.6 mg, 6.9 μmol) in THF (0.6 ml) was added sodium hydride (7.0 mg, 95%, 2.8 mmol) at 0° C. The yellow suspension was stirred for 20 min at 0° C. under argon. A solution of 5-(2-(bromomethyl)phenyl)-3-methyl-1,2,4-oxadiazole in dry THF (0.4 ml) was added and stirring was continued for 2 h at rt. To the reaction mixture was added water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over sodium sulfate, filtered and evaporated to give 64 mg (98%) of a pale brown oil. [1H NMR (600 MHz, DMSO-d6) ♀ ppm 8.84 (s, 1H), 8.05 (d, J=7.9 Hz, 1H), 7.81 (d, J=8.3 Hz, 1H), 7.68 (t, J=7.7 Hz, 1H), 7.55-7.62 (m, 2H), 7.51 (t, J=7.8 Hz, 1H), 7.34-7.41 (m, 1H), 7.27 (d, J=7.7 Hz, 1H), 4.91 (s, 2H), 4.23-4.34 (m, 2H), 3.46 (t, J=11.1 Hz, 2H), 3.26-3.32 (m, 2H), 2.44 (s, 3H), 2.04-2.12 (m, 2H), 1.93-2.01 (m, 2H), 1.83-1.92 (m, 2H), 1.66 (d, J=13.5 Hz, 2H); LCMS RtD=2.63 min, [M+H]+=469.2].

Workup

  1. stirringstirring
  2. waitwas continued for 2 h at rt
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washThe organic phases were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-220d14a8c419453d8a0a81a70f3f09a6
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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