1-Methylimidazole → HCID 178490002, compound

HRID 83833Notes

Reaction equation

HRID 83833 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].[CH3:47][N:48]1[CH:52]=[CH:51][N:50]=[CH:49]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+:50]2[CH:51]=[CH:52][N:48]([CH3:47])[CH:49]=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)([CH3:29])[CH3:28])=[CH:25][N:26]=1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 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 178490002HCID 178490002, compoundYield 16%

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 1-methylimidazole (0.1 mL) in CH3CN was refluxed in sealed tube for 3 h. After cooling and evaporation of volatiles, the residue was purified by column chromatography (DCM/MeOH=5:1) to give the title compound (8 mg, 16% yield). 1H NMR (400 MHz, CD3OD) δ 8.98-8.94 (m, 1H), 7.66 (d, J=1.95 Hz, 1H), 7.61 (t, J=1.73 Hz, 2H), 7.47-7.39 (m, 1H), 7.24 (s, 1H), 6.99-6.89 (m, 1H), 6.83 (t, J=8.63 Hz, 2H), 6.65-6.56 (m, 1H), 6.56-6.48 (m, 1H), 6.32 (dd, J=8.88, 4.80 Hz, 2H), 4.37 (t, J=6.77 Hz, 3H), 4.02 (d, J=1.33 Hz, 3H), 3.95 (s, 4H), 3.73 (d, J=3.60 Hz, 4H), 2.99-2.88 (m, 3H), 2.69 (d, J=3.79 Hz, 14H), 2.15-2.05 (m, 3H), 1.51 (s, 9H); MS (EI) m/z 704 (M+).

Workup

  1. temperaturewas refluxed in sealed tube for 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-6950bf88b8054f92a613f21f3508847f
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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