Dimethylformamide → 10-benzyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

HRID 1290748Notes

Reaction equation

HRID 1290748 reaction equation
[CH:1](=[C:8]1[C:20]2[N:19]3[CH:21]=[CH:22][N:23]=[C:18]3[C:17](=[O:24])[NH:16][C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[H][H]>[Pd].CO>[CH2:1]([CH:8]1[C:20]2[N:19]3[CH:21]=[CH:22][N:23]=[C:18]3[C:17](=[O:24])[NH:16][C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 7034388410-benzylidene-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 1529136610-benzyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneYield 37.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.4 g of 10-benzylidene-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 90 ml of dimethylformamide and 10 ml of methanol is hydrogenated at a temperature in the region of 20° C. at a pressure of 1.9 bar of hydrogen for 3 hours in the presence of 10% palladium on charcoal. The catalyst is then filtered off under inert atmosphere and the solvents are evaporated off. The brown solid obtained (0.37 g) is purified by chromatography on a column of silica (35 g) with a mixture of dichloromethane and methanol (90/10 by volume). After trituration with 5 ml of dichloromethane, filtration and drying at 100° C., 0.15 g of 10-benzyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is obtained, in the form of a beige solid melting above 260° C. (Analysis % calculated C: 76.66, H: 4.82, N: 13.41, O: 5.11, % found C: 76.3, H: 4.6, N: 13.4).

Workup

  1. filtrationThe catalyst is then filtered off under inert atmosphere
  2. customthe solvents are evaporated off
  3. customThe brown solid obtained (0.37 g)
  4. customis purified by chromatography on a column of silica (35 g) with a mixture of dichloromethane and methanol (90/10 by volume)
  5. filtrationAfter trituration with 5 ml of dichloromethane, filtration
  6. customdrying at 100° C.

Sources & evidence

ORD record
ord-4ad5fbcde76c41448dbf87b2f804b08f
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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