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

HRID 2393399Notes

Reaction equation

HRID 2393399 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+].Cl[CH2:29][CH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(OCC)(=O)C.C(O)(=O)C.O>[C:1]([NH:4][C:5]1([CH2:29][CH2:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=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 24758Sodium hydrideHCID 78543(4-Chlorobutyl)benzeneHCID 1529136110-acetamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 18975476(10 RS)-10-acetamido-10-(4-phenylbutyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneYield 1.8%

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 2.7 g of 1-chloro-4-phenylbutane. 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 methanol. 80 mg of (10 RS)-10-acetamido-10-(4-phenylbutyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one are thus obtained in the form of a green solid melting above 260° C. (Analysis, % calculated C: 72.8, H: 5.9, N: 13.6, O: 7.8, % found C: 72.8, H: 6.0, N: 14.1, O: 7.9).

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 methanol

Sources & evidence

ORD record
ord-299c759f84aa46cab7b79f7c2a5da082
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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