Methane → HCID 18975475, compound

HRID 2393377Notes

Reaction equation

HRID 2393377 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.C([O-])(=O)C.[Na+].Cl.[NH2:14][CH:15]1[C:27]2[N:26]3[CH:28]=[CH:29][N:30]=C3[C:24](=[O:31])[NH:23][C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2.C>CN(C)C=O.C(O)=O>[CH:24]([NH:23][CH:22]1[C:27]2[N:26]3[CH:28]=[CH:29][N:30]=[C:6]3[C:5](=[O:7])[NH:14][C:15]=2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]1=2)=[O:31]

Participants

7

Reactant 4

HCID 297MethaneHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 1897547210-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride

Product 1

HCID 18975475HCID 18975475, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 21.4 g of acetic anhydride and 11.5 g of formic acid is heated for 2 hours at a temperature between 50° C. and 60° C., and cooled to 20° C. 0.9 g of anhydrous sodium acetate is then added followed, after dissolution, by 2.75 g of 10-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride. The mixture is stirred for 1 hour at 20° C. and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 50° C. The product obtained (4.3 g) is dissolved in 50 ml of dimethylformamide and, after addition of decolorizing charcoal, the solution is filtered. 200 ml of distilled water are then added to the filtrate and the mixture is stored for 1 hour at a temperature in the region of 5° C. The insoluble product formed is isolated by filtration, washed with 10 ml of distilled water and dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 1.2 g of 10-formamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one are thus obtained, melting at 280° C. (decomposition) (NMR spectrum: [200 MHz; (CD3)2SO-d6 ; δ in ppm]: 6.22 (d, J=8.5 Hz, 1H: --CH-- 10); 7.36 and 7.45 (2 broad t, J=8 Hz, 2H: --H 7 and --H 8); 7.51 and 7.87 (2 broad d, J=8 Hz, 2H: --H 6 and --H 9); 7.58 and 7.64 (2s, 1H each: --H of the imidazole); 8.44 (s, 1H: --CH=O); 8.78 (d, J=8.5 Hz, 1H: --CONH at 10); 12.50 (broad s, 1H: --CONH-- of the ring)).

Workup

  1. temperatureis heated for 2 hours at a temperature between 50° C. and 60° C.
  2. dissolutionafter dissolution
  3. concentrationconcentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 50° C
  4. customThe product obtained (4.3 g)
  5. filtrationthe solution is filtered
  6. addition200 ml of distilled water are then added to the filtrate
  7. waitthe mixture is stored for 1 hour at a temperature in the region of 5° C
  8. customThe insoluble product formed
  9. customis isolated by filtration
  10. washwashed with 10 ml of distilled water
  11. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

Sources & evidence

ORD record
ord-6d3ae5fadb524e9eb030094e7912aa1f
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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