Water → E-dimethylaminomethylene-5H,10H-imidazo[1,2-a)indeno-[1,2-e]pyrazin-4-one

HRID 2393387Notes

Reaction equation

HRID 2393387 reaction equation
[CH3:1][N:2]([CH:4]=[C:5]1[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)[CH3:3].C(OC(N(C)C)N(C)C)(C)(C)C.C1N2C3CC4C=CC=CC=4C=3NC(=O)C2=NC=1.O>CN(C)C=O.CO>[CH3:3][N:2](/[CH:4]=[C:5]1\[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[C:12]2[NH:13][C:14](=[O:21])[C:15]3[N:16]([CH:18]=[CH:19][N:20]=3)[C:17]\1=2)[CH3:1]

Participants

7

Reactant 4

HCID 962WaterHCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneHCID 5714456510-dimethylaminomethylene-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 15291363E-dimethylaminomethylene-5H,10H-imidazo[1,2-a)indeno-[1,2-e]pyrazin-4-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

10-Dimethylaminomethylene-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one may be prepared in the following way: 6.3 g of t-butoxybis(dimethylamino)-methane are added dropwise over 5 minutes, at a temperature in the region of 25° C., to a suspension of 5.5 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in 100 ml of dimethylformamide. After stirring for 30 minutes at the same temperature, the mixture is poured into 500 ml of distilled water and extracted 5 times with 1.5 liters in total of chloroform. The organic extracts are combined, washed with 250 ml of distilled water, dried over anhydrous magnesium sulphate and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 60° C. The product obtained (4.5 g) is suspended in 25 ml of methanol, filtered off, washed twice with 20 ml in total of methanol and dried under reduced pressure (15 mmHg; 2 kPa) at 20° C. The product obtained (4.5 g) is dissolved in 45 ml of boiling dimethyl2formamide and, after cooling, the solution is stored for 4 hours at a temperature in the region of 5° C. The crystals are isolated by filtration, washed successively with 10 ml of dimethylformamide and 10 ml of acetone, and dried to dryness under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 4 g of 10-(E-dimethylaminomethylene-5H,10H-imidazo[1,2-a)indeno-[1,2-e]pyrazin-4-one are thus obtained, melting at 293° C. [NMR spectrum: (200 MHz; DMSO-d6 ; δ in ppm): 3.35 [S 6H: --N(CH3)2 1; 7.18 and 7.28 (2t, J=7.5 Hz, 2H: --H7 and --H8); 7.48 and 7.92 (2d, J=7.5 Hz, 1H each: --H6 and --H9); 7.63 and 8.50 (2 broad s, 1H each: --H of the imidazole); 8.09 (s, 1H: =CH--N); 12.30 (mult., 1H: --NH--)].

Workup

  1. extractionextracted 5 times with 1.5 liters in total of chloroform
  2. washwashed with 250 ml of distilled water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 60° C
  5. customThe product obtained (4.5 g)
  6. filtrationfiltered off
  7. washwashed twice with 20 ml in total of methanol
  8. customdried under reduced pressure (15 mmHg; 2 kPa) at 20° C
  9. customThe product obtained (4.5 g)
  10. temperatureafter cooling
  11. waitthe solution is stored for 4 hours at a temperature in the region of 5° C
  12. customThe crystals are isolated by filtration
  13. washwashed successively with 10 ml of dimethylformamide 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-d410749c29c04c47bc78bc75bdc46d98
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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