3-Fluorobenzenesulfonyl Chloride → WAY 208466 dihydrochloride

HRID 2416757ノート

反応式

HRID 2416757 の反応式
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]=[CH:6]1.[F:15][C:16]1[CH:17]=[C:18]([S:22]([Cl:25])(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1>[N+](C1C=CC=CC=1)([O-])=O.FC(S([O-])(=O)=O)(F)F.[Ag+]>[ClH:25].[ClH:25].[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([S:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([F:15])[CH:17]=2)(=[O:24])=[O:23])=[CH:6]1

参加物

5

反応物 2

HCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 22028178HCID 22028178、化合物

生成物 1

HCID 22028182WAY 208466 dihydrochloride

試薬・触媒・溶媒 2

HCID 76223Silver(I) trifluoromethanesulfonate触媒HCID 7416Nitrobenzene溶媒

反応条件

温度
100 °C

実験手順

A stirred solution of N,N-dimethyl-N-[2-(1H-pyrrolo[2,3-b]pyridin-1-yl)ethyl]amine (1.66 g, 8.8 mmol) in nitrobenzene is treated with 3-fluorophenylsulfonyl chloride (1.88 g, 9.7 mmol) under nitrogen, followed by silver trifluoromethylsulfonate (2.94 g, 11.4 mmol), heated to 100° C. for 22 h, cooled and filtered through a cotton plug. The filtrate is treated with water and saturated aqueous NaHCO3 and extracted with CH2Cl2. The extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed eluting with 2:98 concentrated NH4OH:ethanol, to afford the free amine of the title compound as a viscous oil which solidifies (1.25 g, 41%). The free amine is dissolved in warm ethanol, treated with 4M HCl in dioxane and filtered. The filtercake is dried to give the title product as a pale yellow solid, 1.07 g (29% yield), mp 191-192° C., identified by mass spectral and HNMR analyses.

後処理

  1. temperaturecooled
  2. filtrationfiltered through a cotton plug
  3. additionThe filtrate is treated with water and saturated aqueous NaHCO3
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue is chromatographed
  8. washeluting with 2:98 concentrated NH4OH

出典と根拠

ORDレコード
ord-e90b461a6b8048d7b3e83d662fc1c3d6
出典データセット
uspto-grants-2004_11
特許番号
US06825212B2

反応ノート

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