4-Pyridinecarboxaldehyde → 10-(4-pyridylmethylene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

HRID 1290755Notes

Reaction equation

HRID 1290755 reaction equation
O1C=CC=C1C=[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.C1N2[C:29]3[CH2:40][C:39]4[CH:38]=CC=C[C:34]=4[C:30]=3[NH:31]C(=O)C2=NC=1.[H-].[Na+].N1C=CC(C=O)=CC=1>CS(C)=O>[N:31]1[CH:30]=[CH:34][C:39]([CH:38]=[C:7]2[C:19]3[N:18]4[CH:20]=[CH:21][N:22]=[C:17]4[C:16](=[O:23])[NH:15][C:14]=3[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)=[CH:40][CH:29]=1

Participants

6

Reactant 4

HCID 133894-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneHCID 7034377510-(2-furylmethylene)-5H,10H-imidazo[l,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 6701521310-(4-pyridylmethylene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The procedure is performed as in Example 17 for the preparation of 10-(2-furylmethylene)-5H,10H-imidazo[l,2-a]indeno[1,2-e]pyrazin-4-one, but starting with 2 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 40 ml of dimethyl sulphoxide, 0.64 g of sodium hydride and 1.07 g of 4-pyridinecarboxaldehyde. The crude product (1.5 g) is purified by crystallization in 100 ml of dimethylformamide and 50 ml of methanol to give 1.06 g of 10-(4-pyridylmethylene)-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one, in the form of an orange solid melting above 260° C. (Analysis % calculated C: 73.07, H: 3.87, N: 17.94, O: 5.12, % found C: 72.9, H: 3.7, N: 18.2).

Workup

  1. customThe crude product (1.5 g) is purified by crystallization in 100 ml of dimethylformamide

Sources & evidence

ORD record
ord-fa7a3e9cbfa6445db01af0b0aa0a4912
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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