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Pyridine → 3-cyano-5-(4'-cyano-benzoylamino)-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

HRID 1943122
ノート
印刷プレビュー

反応式

HRID 1943122 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:29]#[N:30])[CH:5]=[C:6]([CH:28]=1)[C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=1[CH3:27])=[O:8].N1C=CC=CC=1.[C:37]([C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1)#[N:38].C(=O)([O-])O.[Na+]>O1CCCC1>[C:29]([C:4]1[CH:5]=[C:6]([CH:28]=[C:2]([NH:1][C:43](=[O:44])[C:42]2[CH:46]=[CH:47][C:39]([C:37]#[N:38])=[CH:40][CH:41]=2)[CH:3]=1)[C:7]([NH:9][C:10]1[C:11]([CH3:27])=[CH:12][C:13]([C:17]([F:26])([C:18]([F:19])([F:20])[F:21])[C:22]([F:23])([F:24])[F:25])=[CH:14][C:15]=1[CH3:16])=[O:8])#[N:30]
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 592269545-amino-3-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

生成物 1

HCID 866397603-cyano-5-(4'-cyano-benzoylamino)-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide収率 71.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-amino-3-cyano-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (0.199 mg, 0.46 mmol) (Example I9) in tetrahydrofuran (3 ml) were added successively pyridine (0.117 ml, 1.45 mmol) and 4-cyano-benzoyl chloride (80 mg, 0.48 mmol). The reaction mixture was stirred for 2 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. B1 of Table B (0.186 g, 71.9% yield). 1H-NMR (400 MHz, CHCl3): 8.45 (s, 1H), 8.36 (s, 1H), 8.27 (s, 1H), 8.00 (m, 3H), 7.84 (m, 2H), 7.63 (s, 1H), 7.37 (s, 2H), 2.34 (s, 6H) ppm.

後処理

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

出典と根拠

ORDレコード
ord-dfb3e581cdbb4238886872c4cfaea386
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08389766B2

反応ノート

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