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 1432912ノート

反応式

HRID 1432912 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8bd1bdda2c7e4237baf58ac55f786eb3
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

読み込み中…