Imidazole → 10-[4-(imidazol-1-yl)butyl]-10-methyl-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one

HRID 2393388Notes

Reaction equation

HRID 2393388 reaction equation
[CH3:1][CH:2]1[C:14]2[N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11](=[O:18])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[H-].[Na+].C[Si](C)(C)Cl.Br[CH2:27][CH2:28][CH:29](Cl)[CH3:30].[NH:32]1[CH:36]=[CH:35][N:34]=[CH:33]1>CN(C)C=O>[N:32]1([CH2:27][CH2:28][CH2:29][CH2:30][C:2]2([CH3:1])[C:14]3[N:13]4[CH:15]=[CH:16][N:17]=[C:12]4[C:11](=[O:18])[NH:10][C:9]=3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]2=3)[CH:36]=[CH:35][N:34]=[CH:33]1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydrideHCID 1897544610-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneHCID 22644751HCID 22644751, compound

Product 1

HCID 1897541110-[4-(imidazol-1-yl)butyl]-10-methyl-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The process is performed as in Example 33 but starting with 0.48 g of 10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 25 ml of dimethylformamide, 0.33 g of 80% sodium hydride, 0.30 ml of trimethylchlorosilane, 0.25 ml of 1-bromo-3-chlorobutane and 0.15 g of imidazole. After chromatography on a column of silica (20 g), eluting with a mixture of chloroform, methanol and 28% aqueous ammonia (90/7/3 by volume), 0.26 g of 10-[4-(imidazol-1-yl)butyl]-10-methyl-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one is obtained in the form of a cream-coloured solid melting at about 160° C. (Analysis, % calculated C: 70.18, H: 5.89, N: 19.48, O: 4.45, % found C: 70.3, H: 6.0, N: 19.6).

Workup

  1. washAfter chromatography on a column of silica (20 g), eluting with a mixture of chloroform, methanol and 28% aqueous ammonia (90/7/3 by volume)

Sources & evidence

ORD record
ord-91bd6f0f34324a14837f30095120fc45
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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