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Ammonium Chloride → N-[5-(4-Fluoro-2-methoxy-phenyl)-pyridazin-4-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide

HRID 403395
ノート
印刷プレビュー

反応式

HRID 403395 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([NH:14][CH3:15])=[CH:10][N:11]=[N:12][CH:13]=2)=[C:4]([O:16][CH3:17])[CH:3]=1.[CH3:18][S:19]([C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:25](Cl)=[O:26])(=[O:21])=[O:20].C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]([CH3:15])[C:25](=[O:26])[C:24]3[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=[C:22]([S:19]([CH3:18])(=[O:21])=[O:20])[CH:23]=3)=[CH:10][N:11]=[N:12][CH:13]=2)=[C:4]([O:16][CH3:17])[CH:3]=1
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 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 866708083-(Methylsulfonyl)-5-(trifluoromethyl)benzoyl chlorideHCID 866984835-(4-fluoro-2-methoxyphenyl)-N-methylpyridazin-4-amine

生成物 1

HCID 71766376N-[5-(4-Fluoro-2-methoxy-phenyl)-pyridazin-4-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide収率 26.7%

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 5-(4-fluoro-2-methoxyphenyl)-N-methylpyridazin-4-amine (27 mg, 116 μmol) in dichloromethane (1 mL) were added 3-(methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride (66.4 mg, 232 mmol) and N,N-diisopropylethylamine (60 mg, 80.9 μL, 463 μmol). The clear, light brown solution was stirred at room temperature for 1.75 h and then poured on saturated aqueous ammonium chloride solution and dichloromethane and the layers were separated. The aqueous layer was extracted three times with dichloromethane. The organic layers were dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100) to give the desired compound as a light brown solid (15 mg; 25%). MS (ESI+): m/z=483.09 ([M+H]+).

後処理

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted three times with dichloromethane
  3. dry with materialThe organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. additiontreated with silica gel
  6. customevaporated
  7. customThe compound was purified by silica gel chromatography on a 10 g column
  8. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100)

出典と根拠

ORDレコード
ord-2b52fa2986fa44508a31d6cb3482726e
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08748434B2

反応ノート

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