Potassium Carbonate → (3s, 5r)-1-(4-Chloro-quinolin-7-ylmethyl)-4-[3-(5-chloro-thiophen-2-yl)-allyl]-3,5-dimethyl-piperazine-2-one

HRID 1432912노트

반응식

HRID 1432912 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH:17]([CH3:19])[NH:16][C@@H:15]([CH3:20])[C:14]3=[O:21])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH:30]=[CH:31][C:32]1[S:33][C:34]([Cl:37])=[CH:35][CH:36]=1>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][C@@H:17]([CH3:19])[N:16]([CH2:29][CH:30]=[CH:31][C:32]4[S:33][C:34]([Cl:37])=[CH:35][CH:36]=4)[C@@H:15]([CH3:20])[C:14]3=[O:21])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 537995313-(5-Chlorothiophen-2-yl)allyl bromideHCID 57284059(3s,5Rs)-1-(4-chloro-quinolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one

생성물 1

HCID 91216935(3s, 5r)-1-(4-Chloro-quinolin-7-ylmethyl)-4-[3-(5-chloro-thiophen-2-yl)-allyl]-3,5-dimethyl-piperazine-2-one수율 27.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The crude (3S,5RS)-1-(4-chloro-quinolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one (69 mg, 0.20 mmol) obtained from above is dissolved in 1 mL of DMF. Potassium carbonate (76 mg, 0.60 mmol) is added followed by the addition of 2-(3-bromopropenyl)-5-chloro-thiophene (56 mg, 0.24 mmol). The reaction is left to stir overnight. The potassium carbonate is filtered off, and the crude material is purified. The two epimers are separated at this stage by preparative thin layer chromatography (80% EtOAc/hexane) to give a major epimer (3S, 5R)-1-(4-chloro-quinolin-7-ylmethyl)-4-[3-(5-chloro-thiophen-2-yl)-allyl]-3,5-dimethyl-piperazine-2-one (25 mg, 26% yield) and a minor epimer (3S, 5S)-1-(4-chloro-quinolin-7-ylmethyl)-4-[3-(5-chloro-thiophen-2-yl)-allyl]-3,5-dimethyl-piperazine-2-one (7 mg, 7.5% yield).

후처리

  1. waitThe reaction is left
  2. filtrationThe potassium carbonate is filtered off
  3. customthe crude material is purified
  4. customThe two epimers are separated at this stage by preparative thin layer chromatography (80% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-8bd1bdda2c7e4237baf58ac55f786eb3
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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