Acetic Acid → 10-acetamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

HRID 1290740Notes

Reaction equation

HRID 1290740 reaction equation
O/[N:2]=[C:3]1\[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[C:10]2[NH:11][C:12](=[O:19])[C:13]3[N:14]([CH:16]=[CH:17][N:18]=3)[C:15]\1=2.C.[C:21](O)(=[O:23])[CH3:22]>O.CN(C)C=O.[Zn]>[C:21]([NH:2][CH:3]1[C:15]2[N:14]3[CH:16]=[CH:17][N:18]=[C:13]3[C:12](=[O:19])[NH:11][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2)(=[O:23])[CH3:22]

Participants

7

Reactant 3

HCID 176Acetic Acid2×HCID 297MethaneHCID 178518651HCID 178518651, compound

Product 1

HCID 1529136110-acetamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 5.25 g of 10-(E-hydroxy-imino)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one and 2.9 g of zinc powder in 100 ml of acetic acid is heated for 2 hours at a temperature between 80° C. and 90° C. After addition of 100 ml of acetic acid, the mixture is filtered and the filtrate is concentrated to dryness under reduced pressure (10 mmHg; 2 kPa) at 65° C. The product obtained (3.8 g) is suspended in 100 ml of distilled water, filtered, washed with 10 ml of distilled water and with 10 ml of acetone and then dried under reduced pressure (15 mmHg; 2 kPa) at 20° C. The product obtained (2 g) is dissolved in 60 ml of boiling dimethylformamide and, after addition of 0.1 g of decolorizing charcoal, the solution is filtered while hot. The filter is washed with 10 ml of boiling dimethylformamide and the filtrate and the combined washings are then stored for 4 hours at a temperature in the region of 20° C. The crystals formed are separated out by filtration, washed successively with 10 ml of dimethylformamide, 10 ml of distilled water and 10 ml of acetone and dried to dryness under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 0.43 g of 10-acetamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is thus obtained, decomposing without melting at 330° C. [N.M.R. spectrum: (200 MHz; DMSO d6 ; δ in ppm): 2.00 (s, 3H: --CO--CH3); 6.13 (d, J=8.5 Hz, 1H: CH--N); 7.35 and 7.48 (2t, J=7.5 Hz, 1H each: --H7 and --H8); 7.48 and 7.85 (2d, J=7.5 Hz, 1H each: --H6 and --H9); 7.58 and 7.65 (2s broad, 1H each: --H of the imidazole); 8.58 (d, J=8.5 Hz, 1H: --NH--COCH3); 12.50 (cplx, 1H: --NH--)].

Workup

  1. temperatureis heated for 2 hours at a temperature between 80° C. and 90° C
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure (10 mmHg; 2 kPa) at 65° C
  4. customThe product obtained (3.8 g)
  5. filtrationfiltered
  6. washwashed with 10 ml of distilled water and with 10 ml of acetone
  7. customdried under reduced pressure (15 mmHg; 2 kPa) at 20° C
  8. customThe product obtained (2 g)
  9. filtrationthe solution is filtered while hot
  10. washThe filter is washed with 10 ml of boiling dimethylformamide
  11. customThe crystals formed
  12. customare separated out by filtration
  13. washwashed successively with 10 ml of dimethylformamide, 10 ml of distilled water and 10 ml of acetone
  14. customdried to dryness under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

Sources & evidence

ORD record
ord-71bccbee2d824964be3b90f31bdfac64
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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