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

HRID 1094519노트

반응식

HRID 1094519 반응식
[C:1]([C:5]1[CH:6]=[C:7]([NH2:18])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]([O:26][C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[C:33]([C:37](Cl)=[O:38])=[CH:32][CH:31]=[CH:30]3)[CH:21]=1.N1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([NH:18][C:37]([C:33]2[C:34]3[C:29](=[CH:28][C:27]([O:26][C:22]4[CH:21]=[C:20]([Cl:19])[N:25]=[CH:24][N:23]=4)=[CH:36][CH:35]=3)[CH:30]=[CH:31][CH:32]=2)=[O:38])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 111393953-(tert-Butyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amineHCID 574551736-(6-Chloropyrimidin-4-yloxy)naphthalene-1-carbonyl chloride

생성물 1

HCID 867615276-(6-Chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid [5-tert-butyl-2-(4-methoxy-phenyl)-2H-pyrazol-3-yl]-amide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

2.9 g (12 mMol) 5-tert-butyl-2-(4-methoxy-phenyl)-2H-pyrazol-3-ylamine and 3.8 g (12 mMol) 6-(6-chloropyrimidin-4-yloxy)-naphthalene-1-carbonyl chloride (described under Step 19.3) are dissolved in 10 ml CH2Cl2 and cooled to 0° C. 0.99 ml (12 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 worked up by addition of 150 ml CH2Cl2 and aq. extraction with sat. Na2CO3 solution. The organic layer is subsequently washed with brine and dried. After removal of the solvents the remaining crude product is purified by flash chromatography (SiO2; hexanes/EtOAc, gradient 3:1 to 2:1) to give the title compound as a yellow solid: m.p.: 163-164° C.

후처리

  1. additionafter complete addition the reaction
  2. temperatureto warm to rt
  3. washThe organic layer is subsequently washed with brine
  4. customdried
  5. customAfter removal of the solvents the remaining crude product
  6. customis purified by flash chromatography (SiO2; hexanes/EtOAc, gradient 3:1 to 2:1)

출처 및 근거

ORD 기록
ord-b6c39370d1c24c26a6d75cb91526190e
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133886B2

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