Ammonium Chloride → 3-Methanesulfonyl-N-methyl-N-[2-(2,2,2-trifluoro-ethoxy)-[3,4']bipyridinyl-3'-yl]-5-trifluoromethyl-benzamide

HRID 878318ノート

反応式

HRID 878318 の反応式
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[C:10]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:11][CH:12]=[CH:13][CH:14]=1.[CH3:21][S:22]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[C:28]([OH:30])=O)(=[O:24])=[O:23].[NH4+].[Cl-]>C(Cl)Cl>[CH3:21][S:22]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[C:28]([N:2]([CH3:1])[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[C:10]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:30])(=[O:23])=[O:24]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 70663341Methyl-[2-(2,2,2-trifluoro-ethoxy)-[3,4]bipyridinyl-3'-yl]-amine

生成物 1

HCID 866708123-Methanesulfonyl-N-methyl-N-[2-(2,2,2-trifluoro-ethoxy)-[3,4']bipyridinyl-3'-yl]-5-trifluoromethyl-benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The title compound was prepared in analogy to example 90, from methyl-[2-(2,2,2-trifluoro-ethoxy)-[3,4]bipyridinyl-3′-yl]-amine and 3-(methylsulfonyl)-5-(trifluoromethyl)-benzoic acid (example 114, intermediate a) after a reaction time of 18 hours. The reaction mixture was poured on saturated aqueous NH4Cl solution and CH2Cl2 and the layers were separated. The aqueous layer was extracted three times with CH2Cl2. The organic layers were dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 20 g column using an MPLC (ISCO) system eluting with EtOAc (isocratic). Further purification by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Colorless foam (41%). MS (ESI): m/z=534.09 [M+H]+.

後処理

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted three times with CH2Cl2
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. additiontreated with silica gel
  6. customevaporated
  7. customThe compound was purified by silica gel chromatography on a 20 g column
  8. washeluting with EtOAc (isocratic)
  9. customFurther purification by preparative HPLC (Gemini NX column)

出典と根拠

ORDレコード
ord-b3608b61431d4628b7e44bc0c32142a5
出典データセット
uspto-grants-2015_03
特許番号
US08987307B2

反応ノート

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