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Pyridine → 6-(6-Chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid [5-tert-butyl-2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-amide

HRID 1094522
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HRID 1094522 반응식
[C:1]([C:5]1[CH:6]=[C:7]([NH2:17])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[N:24]=[CH:23][N:22]=[C:21]([O:25][C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[C:32]([C:36](Cl)=[O:37])=[CH:31][CH:30]=[CH:29]3)[CH:20]=1.N1C=CC=CC=1>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:36]([C:32]2[C:33]3[C:28](=[CH:27][C:26]([O:25][C:21]4[CH:20]=[C:19]([Cl:18])[N:24]=[CH:23][N:22]=4)=[CH:35][CH:34]=3)[CH:29]=[CH:30][CH:31]=2)=[O:37])[N:8]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1049PyridineHCID 20605733-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-amineHCID 574551736-(6-Chloropyrimidin-4-yloxy)naphthalene-1-carbonyl chloride

생성물 1

HCID 866386206-(6-Chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid [5-tert-butyl-2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-amide

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

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온도
0 °C

실험 절차

560 mg (2.4 mMol) 5-tert-butyl-2-(4-fluoro-phenyl)-2H-pyrazol-3-ylamine and 763 mg (2.4 mMol) 6-(6-chloropyrimidin-4-yloxy)-naphthalene-1-carbonyl chloride (see Step 19.3) are dissolved in 5 ml CH2Cl2 and cooled to 0° C. 193 μl (2.4 mMol) Pyridine are added dropwise and after complete addition the reaction is allowed to warm to rt. It is stirred for 2 h at ambient temperature. The reaction is concentrated under reduced pressure and the remaining crude product is purified by flash chromatography (combi-flash, 40 g column; CH2Cl2/MeOH; gradient 0-5% MeOH) to give the title compound as a yellow foam: MS: [M+1]+=517.

후처리

  1. additionafter complete addition the reaction
  2. temperatureto warm to rt
  3. concentrationThe reaction is concentrated under reduced pressure
  4. customthe remaining crude product is purified by flash chromatography (combi-flash, 40 g column; CH2Cl2/MeOH; gradient 0-5% MeOH)

출처 및 근거

ORD 기록
ord-8c2d0500c61544dfaf9e7c63a89d99f1
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08133886B2

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