3-Fluorobenzenesulfonyl Chloride → WAY 208466 dihydrochloride

HRID 731567Notes

Reaction equation

HRID 731567 reaction equation
[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

Participants

5

Reactant 2

HCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 22028178HCID 22028178, compound

Product 1

HCID 22028182WAY 208466 dihydrochloride

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 7416NitrobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1c89d2e9d1e84eebafaa0a006f7958fe
Source dataset
uspto-grants-2009_09
Patent number
US07585873B2

Reaction notes

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