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1-Hydroxybenzotriazole → 2-(6-quinolinyloxy)-2-(ethoxy)-N-(2-methylpent-3-yn-2-yl) acetamide

HRID 1244808
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반응식

HRID 1244808 반응식
Cl.[NH2:2][C:3]([CH3:8])([CH3:7])[C:4]#[C:5][CH3:6].[N:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH:20]([O:24][CH2:25][CH3:26])[C:21](O)=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O.C(N(CC)CC)C>[N:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH:20]([O:24][CH2:25][CH3:26])[C:21]([NH:2][C:3]([CH3:8])([C:4]#[C:5][CH3:6])[CH3:7])=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219231292-Methylpent-3-yn-2-amine hydrochlorideHCID 219231312-(6-Quinolinyloxy)-2-(ethoxy)acetic acid

생성물 1

HCID 692530452-(6-quinolinyloxy)-2-(ethoxy)-N-(2-methylpent-3-yn-2-yl) acetamide수율 88.7%

시약·촉매·용매

3
HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

Triethylamine (0.3 ml) was added to a stirred solution of 4-amino-4-methylpent-2-yne hydrochloride (0.054 g) in N,N-dimethylformamide (2 ml) giving a white suspension. 2-(6-Quinolinoxy)-2-(ethoxy)acetic acid (0.1 g) was added followed by N-(3-dimethylaminopropyl)-N′-ethyl carbodiimide hydrochloride (0.077 g) and a catalytic amount of 1-hydroxybenzotriazole (0.005 g), and the white suspension was stirred at ambient temperature for 18 hours. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulphate and evaporated under reduced pressure to give a yellow oil (0.117 g). The oil was purified by flash chromatography (silica gel; ethyl acetate/hexane, 1:1 by volume) to give the required product (0.096 g) as a colourless oil.

후처리

  1. customgiving a white suspension
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. washThe organic phase was washed with water, saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-9423977cd3bd46c1b6720cb30ab8a361
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07122672B2

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