methyl 5-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluoro-3-methoxyphenyl)-1H-imidazol-2-ylthio)methyl)-2-(3-hydroxyprop-1-ynyl)benzoate → Methyl 5-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluoro-3-methoxyphenyl)-1H-imidazol-2-ylthio)methyl)-2-(3-hydroxypropyl)benzoate

HRID 1627287Notes

Reaction equation

HRID 1627287 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([O:24][CH3:25])[CH:18]=3)[C:15]([S:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([C:38]#[C:39][CH2:40][OH:41])=[C:32]([CH:37]=3)[C:33]([O:35][CH3:36])=[O:34])=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[H][H]>C(O)C.O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([O:24][CH3:25])[CH:18]=3)[C:15]([S:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([CH2:38][CH2:39][CH2:40][OH:41])=[C:32]([CH:37]=3)[C:33]([O:35][CH3:36])=[O:34])=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 66740390methyl 5-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluoro-3-methoxyphenyl)-1H-imidazol-2-ylthio)methyl)-2-(3-hydroxyprop-1-ynyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 66740842Methyl 5-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluoro-3-methoxyphenyl)-1H-imidazol-2-ylthio)methyl)-2-(3-hydroxypropyl)benzoateYield 85%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a Parr bottle charged with methyl 5-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluoro-3-methoxyphenyl)-1H-imidazol-2-ylthio)methyl)-2-(3-hydroxyprop-1-ynyl)benzoate (140 mg, 0.23 mmol) in degassed ethanol (10 mL) was added PtO2 (100 mg). The reaction vessel was pressurized to 60 psi with hydrogen gas and agitated at room temperature for 16 h. After LCMS analysis showed complete conversion, the reaction mixture was filtered through Celite™ and concentrated in vacuo to give the title compound (120 mg, 85%). MS (EI) m/z 619 (MH+).

Workup

  1. filtrationthe reaction mixture was filtered through Celite™
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0887c23482e44319a9929dad136d7753
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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