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Ethyl Acetate → 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-[2-(3-hydroxy-propoxy)-phenyl]-N-methyl-benzamide

HRID 661624
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HRID 661624 반응식
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:19]1[CH:20]=[N:21][C:22]([C:26]#[N:27])=[CH:23][C:24]=1[CH3:25].[C:28]([O-:31])([O-])=O.[K+].[K+].[C:34](OCC)(=O)[CH3:35]>CN(C=O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:34][CH2:35][CH2:28][OH:31])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:19]1[CH:20]=[N:21][C:22]([C:26]#[N:27])=[CH:23][C:24]=1[CH3:25]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 686032284-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide

생성물 1

HCID 686027404-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-[2-(3-hydroxy-propoxy)-phenyl]-N-methyl-benzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide 8-1 (50 mg, 0.13 mmol), 4-bromopropanol (18 μL, 0.2 mmol) and K2CO3 (55 mg, 0.40 mmol) in DMF (0.4 mL) was stirred at room temperature for 14 hrs. Ethyl acetate was added and the combined organic layers were washed with water, dried over Na2SO4, then purified by silica gel column chromatography eluting with ethyl acetate/hexane (2/3) up to 100% EtOAc to yield 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-[2-(3-hydroxy-propoxy)-phenyl]-N-methyl-benzamide (30 mg). Example 1. MS [M+H]+: 436.1; tR=2.19 min. (method 1)

후처리

  1. washthe combined organic layers were washed with water
  2. dry with materialdried over Na2SO4
  3. custompurified by silica gel column chromatography
  4. washeluting with ethyl acetate/hexane (2/3) up to 100% EtOAc

출처 및 근거

ORD 기록
ord-459e6fbdddf140b396671316e398fd3b
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08084614B2

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