Methanol → HCID 18918195, compound

HRID 1290762Notes

Reaction equation

HRID 1290762 reaction equation
N1C=CN=CC=1C=[C:8]1[CH2:24][N:11]2[C:12]3[CH2:23][C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:13]=3[NH:14][C:15](=[O:16])[C:10]2=[N:9]1.C[N:26]([CH3:29])[CH:27]=O.CO.[H][H]>[Pd].C(O)(=O)C>[N:9]1[CH:10]=[CH:29][N:26]=[CH:27][C:8]=1[CH2:24][CH:23]1[C:12]2[N:11]3[CH:24]=[CH:8][N:9]=[C:10]3[C:15](=[O:16])[NH:14][C:13]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:22]1=2

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 86752575HCID 86752575, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18918195HCID 18918195, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3.2 g of 10-(2-pyrazinylmethylene-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 250 ml of dimethylformamide, 50 ml of methanol and 5 ml of acetic acid is hydrogenated at a temperature in the region of 20° C. and a pressure of 1.8 bar of hydrogen, in the presence of 10% palladium on charcoal for 18 hours. The catalyst is filtered off under inert atmosphere and the filtrate is concentrated on a rotary evaporator. On addition of 200 ml of methanol a precipitate is formed which, after trituration in dichloromethane (100 ml), filtration and drying at 60° C. under vacuum (1 mmHg; 0.13 kPa), gives 1.4 g of 10-(2-pyrazinylmethyl)-5H,10H-imidazo[1,2-a]-indeno[1,2-e]pyrazin-4-one in the form of a beige solid melting above 260° C. (Analysis % calculated C: 68.56, H: 4.16, N: 22.21, O: 5.07, % found C: 68.3, H: 3.9, N: 21.9).

Workup

  1. customis hydrogenated at a temperature in the region of 20° C.
  2. filtrationThe catalyst is filtered off under inert atmosphere
  3. concentrationthe filtrate is concentrated on a rotary evaporator
  4. additionOn addition of 200 ml of methanol a precipitate
  5. customis formed which
  6. filtrationafter trituration in dichloromethane (100 ml), filtration
  7. customdrying at 60° C. under vacuum (1 mmHg; 0.13 kPa)

Sources & evidence

ORD record
ord-dda9074c36d640c999359bf7d112fb92
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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