Dimethylformamide → HCID 18918176, compound

HRID 1290759Notes

Reaction equation

HRID 1290759 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=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.CN(C)C=O>[Pd].C(O)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=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

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 70344571HCID 70344571, compound

Product 1

HCID 18918176HCID 18918176, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The procedure is performed as in Example 21, but starting with 0.7 g of 10-(2-pyridylmethylene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 200 ml of dimethylformamide, 5 ml of acetic acid and 70 mg of 10% palladium on charcoal. The crude product (1.1 g) is purified by trituration in a mixture of 10 ml of dichloromethane and 40 ml of ethyl ether, followed by crystallization in 25 ml of dimethylformamide and 40 ml of water. 0.35 g of 10-(2-pyridylmethyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is obtained, in the form of a light beige solid melting above 260° C. (Analysis % calculated C: 72.60, H: 4.49, N: 17.82, O: 5.09, % found C: 72.5, H: 4.6, N: 17.9, O: 5.5).

Workup

  1. customThe crude product (1.1 g) is purified by trituration in a mixture of 10 ml of dichloromethane and 40 ml of ethyl ether
  2. customfollowed by crystallization in 25 ml of dimethylformamide

Sources & evidence

ORD record
ord-07f4f965fe614d919edf7597cbf2d799
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

Loading…