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

HRID 1958655
ノート
印刷プレビュー

反応式

HRID 1958655 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c811bb928bd24ad6a7654a9d5e9e5c21
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08410145B2

反応ノート

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