Dimethylformamide → HCID 15291368, compound

HRID 1290754Notes

Reaction equation

HRID 1290754 reaction equation
[CH:1](=[C:7]1[C:19]2[N:18]3[CH:20]=[CH:21][N:22]=[C:17]3[C:16](=[O:23])[NH:15][C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H][H].CN(C)C=O>[Pd].CO>[CH2:1]([CH:7]1[C:19]2[N:18]3[CH:20]=[CH:21][N:22]=[C:17]3[C:16](=[O:23])[NH:15][C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 70344337HCID 70344337, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15291368HCID 15291368, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.3 g of 10-hexylidene-5H,10H-imidazo[1,2-a]-indeno[1,2-e]pyrazin-4-one are hydrogenated at a temperature in the region of 20° C. and at a pressure of 9.4 bar of hydrogen in the presence of 120 ml of dimethylformamide, 20 ml of methanol and 0.3 g of 10% palladium on charcoal for 17 hours. After filtration of the catalyst under inert atmosphere, the solvents are evaporated off and the crude product (1.2 g) is purified by chromatography on a column of silica (120 g partially deactivated with 2 ml of water), eluting with a mixture of dichloromethane and methanol (90/10 by volume). 0.47 g of 10-hexyl-5H,10H-imidazo[1,2-a]-indeno[1,2-e]pyrazin-4-one is thus obtained, in the form of a beige solid melting at about 185° C. (Analysis % calculated C: 74.24, H: 6.89, N: 13.67, O: 5.20, % found C: 74.3, H: 7.0, N: 13.6).

Workup

  1. filtrationAfter filtration of the catalyst under inert atmosphere
  2. customthe solvents are evaporated off
  3. customthe crude product (1.2 g) is purified by chromatography on a column of silica (120 g
  4. washeluting with a mixture of dichloromethane and methanol (90/10 by volume)

Sources & evidence

ORD record
ord-5c0a7121cf8a44cc85c2e7b48f2f2a41
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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