HCID 178473439, compound → HCID 20384867, compound

HRID 46821Notes

Reaction equation

HRID 46821 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:10]1[N:15]=[C:14]([NH:16][C:17](OCC)=[O:18])[N+:13]([O-:22])=[C:12]([NH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:11]=1)[CH2:2]2>CN(C)C=O>[CH:5]12[CH2:6][CH2:7][CH:1]([CH2:9][CH2:8]1)[CH2:2][N:3]([C:10]1[CH:11]=[C:12]([NH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:13]3[O:22][C:17](=[O:18])[N:16]=[C:14]3[N:15]=1)[CH2:4]2

Participants

3

Reactant 1

HCID 178473439HCID 178473439, compound

Product 1

HCID 20384867HCID 20384867, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.1 G. of diethyl 6-{3-azabicyclo[3.2.2]non-3-yl}-2,4-pyrimidine-dicarbamate-3-oxide are suspended in 50 ml. of dimethylformamide and warmed to 140° C. for 30 minutes under an argon atmosphere. After cooling the solution, the dimethylformamide is distilled off under reduced pressure and the residue is filtered over silica gel. Elution with chloroform and ethanol yields ethyl 5-{3-azabicyclo[3.2.2]non-3-yl}-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]pyrimidine-7-carbamate, having a melting point of 210°-215° C. (decomposition). Analytically pure product is obtained by recrystallization from methylene chloride/ether.

Workup

  1. temperatureAfter cooling the solution
  2. distillationthe dimethylformamide is distilled off under reduced pressure
  3. filtrationthe residue is filtered over silica gel
  4. washElution with chloroform and ethanol

Sources & evidence

ORD record
ord-0205ccad475e40ecb2b6aec0a6a19431
Source dataset
uspto-grants-1979_11
Patent number
US04175190

Reaction notes

Loading…