Methane → 10-amino-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one hydrochloride

HRID 2393383Notes

Reaction equation

HRID 2393383 reaction equation
C([NH:4][C:5]1([CH3:22])[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)(=O)C.C.[ClH:24]>CO>[ClH:24].[NH2:4][C:5]1([CH3:22])[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2

Participants

5

Reactant 3

HCID 297MethaneHCID 313Hydrochloric AcidHCID 1897538710-acetamido-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 1897542610-amino-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 1 g of 10-acetamido-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in 50 ml of 2N hydrochloric acid is boiled for 1 hour 45 minutes and the solution obtained is concentrated to dryness under reduced pressure (1 mmHg; 0.13 kPa) at 70° C. The product obtained (1.15 g) is dissolved in 100 ml of methanol and, after addition of decolorizing charcoal, the solution is filtered. 300 ml of acetone are added and, after storing for 1 hour at 5° C., the solid formed is isolated by filtration, washed twice with 10 ml in total of chilled acetone and dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 0.39 g of 10-amino-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one hydrochloride is thus obtained, decomposing without melting above 260° C. (NMR spectrum: [200 MHz; (CD3)2SO-d6 ; δ in ppm]: 1.97 (s, 3H: --CH3 at 10); 7.48 and 7.55 (2t, J=7.5 Hz, 1H each: --H 7 and --H 8); 7.70 and 8.75 (2 broad s, 1H each: --H of the imidazole); 7.95 and 8.08 (2d, J=7.5 Hz, 1H each: --H 6 and --H 9); 9.39 (mult., 3H: --NH3+Cl- at 10); 12.64 (mult., 1H: --NHCO--)).

Workup

  1. customthe solution obtained
  2. concentrationis concentrated to dryness under reduced pressure (1 mmHg; 0.13 kPa) at 70° C
  3. customThe product obtained (1.15 g)
  4. filtrationthe solution is filtered
  5. addition300 ml of acetone are added
  6. waitafter storing for 1 hour at 5° C.
  7. customthe solid formed
  8. customis isolated by filtration
  9. washwashed twice with 10 ml in total of chilled acetone
  10. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

Sources & evidence

ORD record
ord-37b29d14f3bc43899b07e318c0c44ff0
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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