Methyl p-toluenesulfonate → 3-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenyl)-N,N,N-trimethylprop-2-yn-1-aminium 4-methylbenzenesulfonate

HRID 83841Notes

Reaction equation

HRID 83841 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][C:28]([C:32]#[C:33][CH2:34][N:35]([CH3:37])[CH3:36])=[CH:27][C:26]=3[F:38])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:39][CH3:40].[C:41]1([CH3:52])[CH:46]=[CH:45][C:44]([S:47]([O:50]C)(=[O:49])=[O:48])=[CH:43][CH:42]=1>CCOCC>[CH3:52][C:41]1[CH:42]=[CH:43][C:44]([S:47]([O-:50])(=[O:49])=[O:48])=[CH:45][CH:46]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:26]([F:38])=[CH:27][C:28]([C:32]#[C:33][CH2:34][N+:35]([CH3:41])([CH3:36])[CH3:37])=[CH:29][C:30]=3[F:31])=[N:13][CH:12]=2)([CH3:9])[CH3:10])=[CH:4][C:3]=1[O:39][CH3:40]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonate2×HCID 672365113-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenyl)-N,N-dimethylprop-2-yn-1-amine

Product 1

HCID 867022383-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenyl)-N,N,N-trimethylprop-2-yn-1-aminium 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenyl)-N,N-dimethylprop-2-yn-1-amine (50 mg, 0.09 mmol, 1.0 eq) in Et2O (0.1 mL) was added methyl p-toluenesulfonate. After 1 h, an additional 1.0 eq methyl p-toluenesulfonate was added and the reaction mixture stirred 30 min. The mixture was filtered to provide 3-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenyl)-N,N,N-trimethylprop-2-yn-1-aminium 4-methylbenzenesulfonate (20 mg) as a white crystalline solid: 1H NMR (400 MHz, DMSO) δ 7.52-7.44 (m, 2H), 7.40 (d, J=7.6 Hz, 2H), 7.26 (d, J=8.3 Hz, 1H), 7.19 (s, 1H), 7.12 (d, J=7.8 Hz, 2H), 7.03-6.92 (m, 2H), 6.55 (d, J=2.0 Hz, 1H), 6.51-6.40 (m, 3H), 4.64 (s, 2H), 3.98 (s, 2H), 3.69 (s, 3H), 3.20 (d, J=13.8 Hz, 9H), 2.29 (s, 3H), 1.46 (s, 6H); MS (EI) m/z 598.3 (M+).

Workup

  1. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-1342fbc096b142ea9246f50995c28e95
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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