Acetic Acid → HCID 70202500, compound

HRID 1290764Notes

Reaction equation

HRID 1290764 reaction equation
[CH:1]1[N:5]2[C:6]3[CH2:17][C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:7]=3[NH:8][C:9](=[O:10])[C:4]2=[N:3][CH:2]=1.[OH-].[Na+].[C:20]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:23])[CH:21]=O.C(O)(=O)C>CS(C)=O.CN(C)C=O.O>[C:25]([O:24][C:20]([CH:21]=[C:17]1[C:6]2[N:5]3[CH:1]=[CH:2][N:3]=[C:4]3[C:9](=[O:10])[NH:8][C:7]=2[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]1=2)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneHCID 10986247Tert-butyl 2-oxoacetate

Product 1

HCID 70202500HCID 70202500, compoundYield 25.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

to a solution, cooled to 19° C. and under cover of nitrogen, of 9 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in 180 ml of dimethyl sulphoxide are added 4 g of 60% sodium hydroxide portionwise with stirring. The stirring is continued for 35 minutes and 7.8 g of tert-butyl glyoxylate are added dropwise. After stirring for 18 hours the reaction mixture is treated with 9 ml of acetic acid and 150 ml of water. The suspension is filtered and the insoluble material is washed with water (2×200 ml) and then with acetone (3×100 ml) and dried at 80° C. under reduced pressure. The crude product obtained (5.85 g) is heated to about 90°-10° C. in 300 ml of dimethylformamide and filtered immediately, and 150 ml of methanol and 200 ml of water are added to the filtrate, which is left in the ice compartment of a refrigerator overnight. The crystals formed are filtered off, washed with 20 ml of water and dried at 80° C. under vacuum (2 mmHg; 0.26 kPa) to give 3.4 g of 10-(tert-butoxycarbonylmethylene)-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one, in the form of a red solid melting above 260° C. (Analysis % calculated C: 68.05, H: 5.11, N: 12.53, O: 14.31, % found C: 68.0, H: 5.6, N: 12.5, O: 14.3).

Workup

  1. stirringAfter stirring for 18 hours the reaction mixture
  2. filtrationThe suspension is filtered
  3. washthe insoluble material is washed with water (2×200 ml)
  4. dry with materialwith acetone (3×100 ml) and dried at 80° C. under reduced pressure
  5. customThe crude product obtained (5.85 g)
  6. filtrationfiltered immediately
  7. addition150 ml of methanol and 200 ml of water are added to the filtrate, which
  8. waitis left in the ice compartment of a refrigerator overnight
  9. customThe crystals formed
  10. filtrationare filtered off
  11. washwashed with 20 ml of water
  12. customdried at 80° C. under vacuum (2 mmHg; 0.26 kPa)

Sources & evidence

ORD record
ord-cdbaa3567f614a0790706fe84ef1d8b0
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

Loading…