Dimethyl Sulfoxide → (10 RS)-10-acetamido-10-(3-phenylpropyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e)pyrazin-4-one

HRID 2393397Notes

Reaction equation

HRID 2393397 reaction equation
[C:1]([NH:4][CH:5]1[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)(=[O:3])[CH3:2].CS(C)=O.[H-].[Na+].Br[CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(OCC)(=O)C.C(O)(=O)C.O>[C:1]([NH:4][C:5]1([CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 1529136110-acetamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 70202950(10 RS)-10-acetamido-10-(3-phenylpropyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e)pyrazin-4-one

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The process is performed as in Example 44 but starting with 3 g of (10 RS)-10-acetamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 70 ml of dimethyl sulphoxide, 1.2 g of an 80% suspension of sodium hydride in oil and 2.6 ml of 1-bromo-3-phenylpropane. The reaction medium is poured into a mixture of 250 g of ice, 435 ml of distilled water and 6 ml of acetic acid. 200 ml of ethyl acetate are added to the suspension obtained and the mixture is stirred, followed, after separation of the phases once settling has taken place, by removal of the ethyl acetate. The operation is repeated once. The precipitate is filtered off on a sinter funnel. The solid is crystallized from 200 ml of methanol. 390 mg of (10 RS)-10-acetamido-10-(3-phenylpropyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e)pyrazin-4-one are obtained in the form of a green solid melting above 260° C. (Analysis, % calculated C: 72.3, H: 5.6, N: 14.0; % found C: 72.2, H: 5.5, N: 14.2).

Workup

  1. customobtained
  2. customafter separation of the phases
  3. customby removal of the ethyl acetate
  4. filtrationThe precipitate is filtered off on a sinter funnel
  5. customThe solid is crystallized from 200 ml of methanol

Sources & evidence

ORD record
ord-5041c561ffb94185b83a7c67f9a4e205
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

Loading…