Sodium hydride → HCID 67015148, compound

HRID 2393368Notes

Reaction equation

HRID 2393368 reaction equation
C(C1C=CC=C[C:5]=1[CH:6]=[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.[CH:28]1[N:32]2C3CC4C=CC=CC=4C=3NC(=O)[C:31]2=[N:30][CH:29]=1.CN1C=CN=C1C=O.[H-].[Na+]>CS(C)=O>[CH3:31][N:30]1[CH:29]=[CH:28][N:32]=[C:5]1[CH:6]=[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

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneHCID 70205095HCID 70205095, compound

Product 1

HCID 67015148HCID 67015148, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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 4.46 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one, 80 ml of dimethyl sulphoxide, 2.6 g of 1-methyl-2-formylimidazole and 1.44 g of 80% sodium hydride. After treatment of the reaction mixture with 80 ml of water and 3 ml of acetic acid, the suspension is filtered and the red solid obtained is washed with methanol and air-dried to give 5 g of 10-[(1-methylimidazol-2-yl)methylene]-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one. The dihydrochloride is formed by adding 3 ml of 3N hydrochloric acid solution in-ethyl ether to a suspension of 1.5 g of crude base in 50 ml of methanol. The yellow precipitate formed is filtered off and dried at 60° C. under vacuum (1 mmHg; 0.13 kPa). 1.75 g of 10-[(1-methylimidazol-2-yl)methylene]-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one dihydrochloride are obtained, melting above 260° C. (Analysis, % calculated C: 55.68, H: 3.89, ° Cl: 18.26, N: 18.04, O: 4.12, % found C: 55.8, H: 3.9, N: 17.9).

Workup

  1. filtrationAfter treatment of the reaction mixture with 80 ml of water and 3 ml of acetic acid, the suspension is filtered
  2. customthe red solid obtained
  3. washis washed with methanol
  4. customair-dried

Sources & evidence

ORD record
ord-4f06d9b9e4a64a21a7398507fcd99944
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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