Dimethylformamide → HCID 18918174, compound

HRID 1290753Notes

Reaction equation

HRID 1290753 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=[C:10]2[C:22]3[N:21]4[CH:23]=[CH:24][N:25]=[C:20]4[C:19](=[O:26])[NH:18][C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O>[Pd].CO>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[C:22]3[N:21]4[CH:23]=[CH:24][N:25]=[C:20]4[C:19](=[O:26])[NH:18][C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 70344429HCID 70344429, compound

Product 1

HCID 18918174HCID 18918174, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The procedure is performed as in Example 13, but starting with 3.9 g of 10-(phenylpropylidene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 180 ml of dimethylformamide, 20 ml of methanol and 0.5 g of 10% palladium on charcoal. The crude product (3.8 g) is purified by chromatography on a column of silica (380 g partially deactivated with 10 ml of water), eluting with a mixture of dichloromethane and methanol (90/10 by volume). After trituration in 10 ml of dichloromethane, filtration and drying at 100° C., 1.1 g of 10-(phenylpropyl)-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one are obtained, in the form of a beige solid melting at 232° C.

Workup

  1. customThe crude product (3.8 g) is purified by chromatography on a column of silica (380 g
  2. washeluting with a mixture of dichloromethane and methanol (90/10 by volume)
  3. filtrationAfter trituration in 10 ml of dichloromethane, filtration
  4. customdrying at 100° C.

Sources & evidence

ORD record
ord-4f2290016751465488c286a32d2af694
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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