HCID 70205095, compound → HCID 18975482, compound

HRID 2393363Notes

Reaction equation

HRID 2393363 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH:6]=[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)([OH:3])=[O:2]>CN(C)C=O.CO.[Pd]>[C:1]([C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][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)([OH:3])=[O:2]

Participants

5

Reactant 1

HCID 70205095HCID 70205095, compound

Product 1

HCID 18975482HCID 18975482, compoundYield 27.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 8 g of 10-(2-carboxybenzylidene)-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one in 350 ml of dimethylformamide and 50 ml of methanol is hydrogenated in the presence of 1 g of 10% palladium-on-charcoal for 20 hours at 10 bar and at a temperature in the region of 20° C. The reaction mixture is filtered on clarcel and the filtrate is evaporated under reduced pressure. The beige-coloured residue obtained is triturated with 200 ml of boiling methanol, filtered and dried at 100° C. under vacuum (1 mmHg; 0.13 kPa); 2.2 g of 10-(2-carboxy-benzyl)-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one are obtained in the form of an off-white solid melting above 260° C. (Analysis, % calculated C: 70.58, H: 4.23, N: 11.76, O: 13.43, % found C: 70.6, H: 4.3, N: 12.1).

Workup

  1. filtrationThe reaction mixture is filtered on clarcel
  2. customthe filtrate is evaporated under reduced pressure
  3. customThe beige-coloured residue obtained
  4. customis triturated with 200 ml of boiling methanol
  5. filtrationfiltered
  6. customdried at 100° C. under vacuum (1 mmHg; 0.13 kPa)

Sources & evidence

ORD record
ord-9a528b9a758a4170905049251306c808
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

Loading…