Water → HCID 70202463, compound

HRID 2393415Notes

Reaction equation

HRID 2393415 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.[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O.[H-].[Na+].O>CS(C)=O.CN(C)C=O.CO.C(O)(=O)C>[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[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

Participants

9

Reactant 4

HCID 962Water2×HCID 24758Sodium hydrideHCID 680093-FluorobenzaldehydeHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 70202463HCID 70202463, compoundYield 12%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolvent2×HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension, maintained under a nitrogen atmosphere and at a temperature in the region of 20° C., of 2.2 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in 45 ml of anhydrous dimethyl sulphoxide are added 1.34 g of 3-fluorobenzaldehyde and then, over 5 minutes, 0.72 g of 80% sodium hydride. The mixture is stirred for 15 hours at the same temperature, followed by slow addition of 45 ml of distilled water and 12 ml of acetic acid. The insoluble product formed is isolated by filtration, washed with distilled water and air-dried. The product obtained (2.6 g) is chromatographed on a column of neutral silica gel, eluting with a dichloromethane/methanol mixture (90/10 by volume). The fractions containing the expected product are concentrated to dryness and the product obtained (1.6 g) is dissolved in 100 ml of dimethylformamide at 100° C. 30 ml of distilled water are then added and the solution is cooled to a temperature in the region of 20° C. The insoluble product formed is isolated by filtration, washed 3 times with 15 ml in total of distilled water and air-dried. The product obtained (0.86 g) is stirred in suspension in 20 ml of boiling methanol and, after cooling, is isolated by filtration, washed with 5 ml of methanol and air-dried. The product obtained (0.56 g) is dissolved in a boiling mixture of 30 ml of acetic acid and 40 ml of dimethylformamide and, after cooling to a temperature in the region of 5° C., the insoluble product formed is isolated by filtration, washed twice with 10 ml in total of acetic acid and twice with 10 ml in total of isopropyl ether, and then dried under reduced pressure (1 mmHg; 0.13 kPa) at 60° C. 0.39 g of 10-(3-fluorobenzylidene)-5H,10H-imidazo[1,2-a]indeno-(1,2-e]pyrazin-4-one is thus obtained, melting at 360° C. (decomposition) (Analysis, % calculated C: 72.94, H: 3.67, F: 5.77, N: 12.76, O: 4.86, % found C: 73.1, H: 3.0, N: 12.5).

Workup

  1. customThe insoluble product formed
  2. customis isolated by filtration
  3. washwashed with distilled water
  4. customair-dried
  5. customThe product obtained (2.6 g)
  6. customis chromatographed on a column of neutral silica gel
  7. washeluting with a dichloromethane/methanol mixture (90/10 by volume)
  8. additionThe fractions containing the expected product
  9. concentrationare concentrated to dryness
  10. customthe product obtained (1.6 g)
  11. customThe insoluble product formed
  12. customis isolated by filtration
  13. washwashed 3 times with 15 ml in total of distilled water
  14. customair-dried
  15. customThe product obtained (0.86 g)
  16. temperatureafter cooling
  17. customis isolated by filtration
  18. washwashed with 5 ml of methanol
  19. customair-dried
  20. customThe product obtained (0.56 g)
  21. temperatureafter cooling to a temperature in the region of 5° C.
  22. customthe insoluble product formed
  23. customis isolated by filtration
  24. washwashed twice with 10 ml in total of acetic acid and twice with 10 ml in total of isopropyl ether
  25. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 60° C

Sources & evidence

ORD record
ord-3b6fb3f2588848a1bc87845a47a6119e
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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