Dimethylformamide → 10-(3-pyridylmethyl)-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one

HRID 1290758Notes

Reaction equation

HRID 1290758 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[C:8]2[C:20]3[N:19]4[CH:21]=[CH:22][N:23]=[C:18]4[C:17](=[O:24])[NH:16][C:15]=3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=3)[CH:2]=1.CN(C)C=O>[Pd].C(O)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]2[C:20]3[N:19]4[CH:21]=[CH:22][N:23]=[C:18]4[C:17](=[O:24])[NH:16][C:15]=3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=3)[CH:2]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 5728636210-(3-pyridylmethylene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 1891815310-(3-pyridylmethyl)-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-oneYield 37.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The procedure is performed as in Example 21, but starting with 1 g of 10-(3-pyridylmethylene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 150 ml of dimethylformamide, 5 ml of acetic acid and 0.1 g of 10% palladium on charcoal. 0.38 g of 10-(3-pyridylmethyl)-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one is obtained, in the form of an off-white solid melting above 260° C. (Analysis % calculated C: 72.60, H: 4.49, N: 17.82, O: 5.09, % found C: 72.3, H: 4.8, N: 17.8, O: 5.4).

Sources & evidence

ORD record
ord-8eed9939a3b54527bf63771d9c3409ab
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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