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Pyridine → N-(3-(5-(3,5-dichlorophenyl)-4,5-dihydro-5-trifluoromethyl-3-isoxazolyl)phenyl)-4-cyanobenzamide

HRID 1958655
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HRID 1958655 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:21]([F:24])([F:23])[F:22])[O:13][N:12]=[C:11]([C:14]3[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C=CC=CC=1.[C:31]([C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)#[N:32].C(=O)([O-])O.[Na+]>O1CCCC1>[C:31]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:11]3[CH2:10][C:9]([C:4]4[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=4)([C:21]([F:22])([F:24])[F:23])[O:13][N:12]=3)[CH:15]=2)=[O:38])=[CH:35][CH:34]=1)#[N:32]
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참가 물질

6

반응물 4

HCID 1049PyridineHCID 801724-Cyanobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 593556813-(5-(3,5-Dichlorophenyl)-4,5-dihydro-5-trifluoromethyl-3-isoxazolyl)aniline

생성물 1

HCID 59549496N-(3-(5-(3,5-dichlorophenyl)-4,5-dihydro-5-trifluoromethyl-3-isoxazolyl)phenyl)-4-cyanobenzamide수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenylamine (0.300 mg, 0.79 mmol) (Example I3) in tetrahydrofuran (4 ml) was added pyridine (0.128 ml, 1.59 mmol). 4-Cyano-benzoyl chloride (0.176 g, 1 mmol) was added under vigorous stirring at ambient temperature. The reaction mixture was stirred for 3 hours at ambient temperature. Aqueous sodium hydrogen carbonate (saturated) was added and the phases were separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1) to give Compound No. A4 of Table A (0.342 g, 85% yield). 1H-NMR (400 MHz, CDCl3): 8.68 (s, 1H), 8.10 (s, 1H), 8.0 (m, 2H), 7.75 (m, 3H), 7.49 (s, 2H), 7.42 (m, 3H), 4.12 (d, 1H), 3.72 (d, 1H).

후처리

  1. stirringThe reaction mixture was stirred for 3 hours at ambient temperature
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1)
  7. customto give Compound No

출처 및 근거

ORD 기록
ord-c811bb928bd24ad6a7654a9d5e9e5c21
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410145B2

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