Potassium Carbonate → N-(2-Chlorobenzyl)-2-[3-(3-chloro-5-cyanophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]-N-methylacetamide

HRID 1952362노트

반응식

HRID 1952362 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:12](=[O:21])[NH:13][CH:14]=[CH:15][C:16]=2[C:17]([F:20])([F:19])[F:18])[CH:9]=1)[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][C:30]([N:32]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[Cl:41])[CH3:33])=[O:31]>CN(C)C=O>[Cl:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[CH2:34][N:32]([CH3:33])[C:30](=[O:31])[CH2:29][N:13]1[CH:14]=[CH:15][C:16]([C:17]([F:18])([F:19])[F:20])=[C:11]([O:10][C:8]2[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([Cl:1])[CH:9]=2)[C:12]1=[O:21]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 432370062-Chloro-N-(2-chlorobenzyl)-N-methylacetamideHCID 584600483-Chloro-5-((1,2-dihydro-2-oxo-4-(trifluoromethyl)-3-pyridinyl)oxy)benzonitrile

생성물 1

HCID 42644875N-(2-Chlorobenzyl)-2-[3-(3-chloro-5-cyanophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]-N-methylacetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a flask charged with 3-chloro-5-{[2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile (3C, 0.020 g, 0.064 mmol) and potassium carbonate (0.0088 g, 0.064 mmol) was added 2-chloro-N-(2-chlorobenzyl)-N-methylacetamide in dimethylformamide (0.75 mL). The reaction mixture was allowed to stir at room temperature. After 1.5 hours, the reaction mixture was filtered and the filtrate was purified by preparative HPLC Phenomenex Luna C18 100A 10μ, eluting with 30-95% MeCN/H2O+0.1% TFA. and lyophilized to yield the title compound. 1H NMR (DMSO-d6) δ 7.90-7.84 (m, 1H), 7.76-7.74 (m, 1H), 7.54-7.43 (m, 3H), 7.42-7.32 (m, 1H), 7.31-7.26 (m, 2H), 7.23-7.19 (m, 1H), 6.68-6.62 (m, 1H), 5.09 (s, 1.35H), 4.80 (s, 0.65H), 4.72 (s, 0.65H), 4.59 (s, 1.35H), 3.06 (s, 2H), 2.82 (s, 1H). HRMS (M+1)=510.0591.

후처리

  1. filtrationthe reaction mixture was filtered
  2. customthe filtrate was purified by preparative HPLC Phenomenex Luna C18 100A 10μ
  3. washeluting with 30-95% MeCN/H2O+0.1% TFA

출처 및 근거

ORD 기록
ord-0f4846f2399349b2b6ff9eb166cfea7f
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404856B2

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