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

HRID 878378ノート

反応式

HRID 878378 の反応式
ClC1C(C2C=CN=CC=2NC)=CC=CN=1.F[C:17]1[CH:22]=[CH:21]C=[C:19](OC)[C:18]=1[C:25]1[CH:30]=[CH:29][N:28]=[CH:27][C:26]=1[N:31]([CH2:48]C(F)(F)F)[C:32](=[O:47])[C:33]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([S:43]([CH3:46])(=[O:45])=[O:44])[CH:34]=1.CCN(C(C)C)C(C)C.[NH4+:62].[Cl-:63]>C(Cl)Cl>[Cl:63][C:19]1[C:18]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[N:31]([CH3:48])[C:32](=[O:47])[C:33]2[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([S:43]([CH3:46])(=[O:44])=[O:45])[CH:34]=2)=[CH:17][CH:22]=[CH:21][N:62]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 86670807N-[4-(2-Fluoro-6-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide2 回HCID 866708262-chloro-N-methyl-3,4'-bipyridin-3'-amine

生成物 1

HCID 86670825N-(2-Chloro-[3,4']bipyridinyl-3'-yl)-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-chloro-N-methyl-3,4′-bipyridin-3′-amine (0.2 g, 910 μmol, example 313, intermediate a) in CH2Cl2 (5 mL) were added 3-(methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride (522 mg, 1.82 mmol, example 223, intermediate d) and DIPEA (471 mg, 636 μL, 3.64 mmol) and the light yellow solution was stirred at room temperature for 16 hours. The reaction mixture was poured on saturated aqueous NH4Cl solution and CH2Cl2 and the layers were separated. The aqueous layer was extracted four times with CH2Cl2. The organic layers dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light brown foam (0.393 g; 91%). MS (ESI): m/z=470.06 [M+H]+.

後処理

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted four times with CH2Cl2
  3. dry with materialThe organic layers dried over MgSO4
  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:EtOAc (100:0 to 0:100)

出典と根拠

ORDレコード
ord-fb35a5159b8146c8ba4a4a5f3c2aaa82
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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