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

HRID 2393399노트

반응식

HRID 2393399 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-299c759f84aa46cab7b79f7c2a5da082
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05807859

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