Sodium hydride → HCID 178525390, compound

HRID 2393373Notes

Reaction equation

HRID 2393373 reaction equation
C(C1C=CC=CC=1C=[C:7]1[C:19]2[N:18]3[CH:20]=[CH:21][N:22]=[C:17]3[C:16](=[O:23])[NH:15][C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)(O)=O.C1N2C3CC4C=CC=CC=4C=3NC(=O)C2=NC=1.O=[CH:46][CH2:47][CH2:48][CH2:49][C:50]([O:52]CC)=[O:51].[H-].[Na+]>C(O)C.[OH-].[Na+].C(O)(=O)C.O.CS(C)=O>[OH:23][C:16]1[C:17]2[N:18]([CH:20]=[CH:21][N:22]=2)[C:19]2[C:7](=[CH:46][CH2:47][CH2:48][CH2:49][C:50]([OH:52])=[O:51])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]=2[N:15]=1

Participants

10

Reactant 4

HCID 24758Sodium hydrideHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneHCID 11137279Ethyl 5-oxopentanoateHCID 70205095HCID 70205095, compound

Product 1

HCID 178525390HCID 178525390, compound

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

The process is performed as in Example 3 for the preparation of 10-(2-carboxybenzylidene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one but starting with 3.3 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one, 66 ml of dimethyl sulphoxide, 2.35 g of ethyl 5-oxopentanoate and 1.06 g of sodium hydride. After treatment of the reaction mixture with water (66 ml) and with acetic acid (6.6 ml), the suspension obtained is filtered, the insoluble product is washed with water (50 ml), with methanol (25 ml) and then with ethyl ether (2×25 ml) and dried at 60° C. under reduced pressure. The solid obtained is suspended in a mixture of 70 ml of ethanol and 6 ml of 1ON sodium hydroxide, filtered off, washed with ethanol and purified by dissolution in 15 ml of water and precipitation with 15 ml of IN hydrochloric acid. The precipitate is filtered off, washed with water (2×10 ml), triturated at the reflux of methanol (200 ml), filtered off and dried. 0.4 g of 5-(4-hydroxyimidazo[1,2-a]indeno-[1,2-e]pyrazin-10-ylidene]pentanoic acid is obtained, which product is converted into the disodium salt of formula C18H13N3O3Na2 (Analysis, % calculated C: 59.18, H: 3.59, N: 11.50, O: 13.14, Na: 12.59, % found C 58.8, H: 3.4, N: 11.5).

Workup

  1. filtrationis filtered
  2. washthe insoluble product is washed with water (50 ml), with methanol (25 ml)
  3. dry with materialwith ethyl ether (2×25 ml) and dried at 60° C. under reduced pressure
  4. customThe solid obtained
  5. filtrationfiltered off
  6. washwashed with ethanol
  7. custompurified by dissolution in 15 ml of water
  8. customprecipitation with 15 ml of IN hydrochloric acid
  9. filtrationThe precipitate is filtered off
  10. washwashed with water (2×10 ml)
  11. customtriturated at the
  12. temperaturereflux of methanol (200 ml)
  13. filtrationfiltered off
  14. customdried

Sources & evidence

ORD record
ord-570eca46565645c4a8f9e48ae5d39683
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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