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HCID 22032839, 화합물 → HCID 86587160, 화합물

HRID 1791387
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HRID 1791387 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](Cl)=[O:11])[CH:2]=1.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[CH:22]=[N:23][NH2:24]>C1COCC1.CCN(CC)CC>[F:17][C:18]([F:28])([F:29])[C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[CH:22]=[N:23][NH:24][C:10]([C:9]1[C:8]([O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:16][CH:15]=[CH:14][CH:13]=1)=[O:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 22032839HCID 22032839, 화합물HCID 69356013HCID 69356013, 화합물

생성물 1

HCID 86587160HCID 86587160, 화합물수율 55%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8471Triethylamine용매

실험 절차

To a stirred solution of 2-(pyridin-3-yloxy)-nicotinic acid (0.432 g, 2.0 mmol) in THF (15 mL) at 0° C. was added oxalylchloride (2 mL, 2M in CH2Cl2, 4.0 mmol) dropwise. The solution was stirred at room temperature for 3 h. The solvent was evaporated in vacuo to yield 2-(pyridin-3-yloxy)-nicotinoyl chloride as a solid. To a solution of 2-(pyridin-3-yloxy)-nicotinoyl chloride in 15 mL THF was added 3-trifluoromethyl-benzylidene-hydrazine (0.376 g, 2.0 mmol) in 5 mL THF and 1 mL Et3N at 0° C. The reaction mixture was refluxed for 6 h and the solvent was evaporated. The residue was purified by chromatography with EtOAc:hexanes, 1:2, yielding (0.425 g, 55%) of the title compound. 1H NMR (DMSO-d6): 12.20 (s, 1H), 8.70 (s, 1H), 8.37 (s, 1H), 8.24 (s, 1H), 8.21 (d, J=7.8 Hz, 1H), 8.01 (d, J=7.5 Hz, 1H), 7.90 (m, 2H), 7.78 (t, J=7.8 Hz, 1H), 7.41 (m, 2H), 6.43 (m, 2H).

후처리

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. customthe solvent was evaporated
  3. customThe residue was purified by chromatography with EtOAc

출처 및 근거

ORD 기록
ord-b85e4707b7e14bc5916c2f41fb6f0b20
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07074813B2

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