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4-(1-Pyrrolidinyl)piperidine → Methyl 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245236
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인쇄 미리보기

반응식

HRID 245236 반응식
Br[CH2:2][C:3]1[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([O:15][CH3:16])=[O:14])=[CH:10][C:9]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:8][CH:7]=2.[N:31]1([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:35][CH2:34][CH2:33][CH2:32]1>C(#N)C>[CH3:20][S:17]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=1)[C:3]([CH2:2][N:39]1[CH2:40][CH2:41][CH:36]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:37][CH2:38]1)=[C:12]2[C:13]([O:15][CH3:16])=[O:14])(=[O:18])=[O:19]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 67383823Methyl 3-(bromomethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

생성물 1

HCID 67419178Methyl 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate수율 93.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

An orange suspension of methyl 3-(bromomethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.068 g, 2.126 mmol) and 4-(1-pyrrolidinyl)piperidine (0.492 g, 3.19 mmol) in acetonitrile (14.17 ml) was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was absorbed onto florisil and was purified via column chromatography (ISCO, 12 g silica, 5-10% methanol/dichloromethane) to give methyl 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.14 g, 88% yield). MS (m/z) 576.2 (M+H+).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was absorbed onto florisil
  3. customwas purified via column chromatography (ISCO, 12 g silica, 5-10% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-ef170657c88b47cebaadfc95a8b37adf
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658636B2

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