Methanol → HCID 9906742, compound

HRID 2393365Notes

Reaction equation

HRID 2393365 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[CH:7]=[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)([OH:3])=[O:2].CO>[Pd].CN(C)C=O>[C:1]([C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[CH2:7][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)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 57285833HCID 57285833, compound

Product 1

HCID 9906742HCID 9906742, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

The process is performed as in Example 3 but starting with 6.9 g of 10-(3-carboxybenzylidene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 50 ml of methanol, 250 ml of dimethylformamide and 0.7 g of 10% palladium-on-charcoal. After evaporation of the solvents and trituration of the solid obtained with 100 ml of methanol, 5.1 g of 10-(3-carboxybenzyl)-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., which product is converted into the sodium salt of formula C21 H14N3O3Na (Analysis, % calculated C 66.49, H: 3.72, N: 11.08, O: 12.65, Na : 6.06, % found C: 66.6, H: 3.7, N: 10.9).

Workup

  1. customAfter evaporation of the solvents and trituration of the solid

Sources & evidence

ORD record
ord-d70627aba03f4865a9a1d9af372d30c3
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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