Pyridine → 1-(3-(3-chloro-5-fluoro-4-((5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)phenylsulfonamido)propyl)pyridinium methanesulfonate

HRID 83832Notes

Reaction equation

HRID 83832 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][CH2:8][NH:9][S:10]([C:13]1[CH:18]=[C:17]([F:19])[C:16]([CH2:20][S:21][C:22]2[N:23]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[C:24]([C:27]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([O:37][CH3:38])[CH:31]=3)([CH3:29])[CH3:28])=[CH:25][N:26]=2)=[C:15]([Cl:46])[CH:14]=1)(=[O:12])=[O:11])(=[O:4])=[O:3].[N:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CC#N>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[Cl:46][C:15]1[CH:14]=[C:13]([S:10]([NH:9][CH2:8][CH2:7][CH2:6][N+:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)(=[O:11])=[O:12])[CH:18]=[C:17]([F:19])[C:16]=1[CH2:20][S:21][C:22]1[N:23]([C:39]2[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=2)[C:24]([C:27]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[C:32]([O:37][CH3:38])[CH:31]=2)([CH3:28])[CH3:29])=[CH:25][N:26]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 867022233-(3-chloro-5-fluoro-4-((5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)phenylsulfonamido)propyl methanesulfonate

Product 1

HCID 867022241-(3-(3-chloro-5-fluoro-4-((5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)phenylsulfonamido)propyl)pyridinium methanesulfonateYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(3-chloro-5-fluoro-4-((5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)phenylsulfonamido)propyl methanesulfonate (50 mg, 0.064 mmol) and pyridine (0.1 mL, 12.8 mmol) in CH3CN was refluxed in sealed tube 3 h. After cooling and evaporation of volatiles, the residue was purified by column chromatography (DCM/MeOH=5:1) to give the title compound (36 mg, 80% yield). 1H NMR (400 MHz, CD3OD) δ 9.21 (d, J=5.71 Hz, 2H), 8.40 (t, J=7.79 Hz, 1H), 8.07-7.98 (m, 2H), 7.49 (s, 1H), 7.29 (dd, J=8.90, 1.32 Hz, 1H), 7.17 (s, 1H), 6.86 (dd, J=11.02, 8.48 Hz, 1H), 6.80 (dd, J=11.65, 5.39 Hz, 2H), 6.55 (dd, J=8.10, 2.16 Hz, 1H), 6.47 (ddd, J=8.34, 4.11, 2.22 Hz, 1H), 6.44-6.38 (m, 2H), 4.99 (t, J=6.27 Hz, 2H), 4.07 (s, 2H), 2.92-2.82 (m, 2H), 2.63 (s, 3H), 2.25-2.12 (m, 2H), 3.75 (s, 3H), 1.49 (s, 7H); MS (EI) m/z 701 (M+).

Workup

  1. temperaturewas refluxed in sealed tube 3 h
  2. temperatureAfter cooling
  3. customevaporation of volatiles
  4. customthe residue was purified by column chromatography (DCM/MeOH=5:1)

Sources & evidence

ORD record
ord-c40a9dfdbde84e06b1f142745502d58b
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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