1-Phenethylamine, (-)- → HCID 9848045, compound

HRID 2298423Notes

Reaction equation

HRID 2298423 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[N:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13](S(C)(=O)=O)[N:12]=2)[CH:10]=1)=[O:5])[CH3:2].[CH3:31][C@H:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[N:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:39][C@H:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH3:31])[N:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 18338458HCID 18338458, compound

Product 1

HCID 9848045HCID 9848045, compound

Procedure

A solution of 1-(2-methylsulfonylpyrimidin4-yl)-2-(3-trifluoromethylphenyl)-1H-imidazole4-carboxylic acid ethyl ester (4.5 g, 0.0102 mol) in (S)-α-methylbenzylamine (20 mL) was stirred at room temperature for 30 min. The reaction was partitioned between 300 mL ethyl acetate and 300 mL pH 4.5 citric acid solution (buffered with NaOH) and the ethyl acetate dried over anhydrous magnesium sulfate. Concentration of the ethyl acetate afforded 4.8 g of the title compound. A portion of this material was purified by reverse phase HPLC on C18 silica eluting with a gradient of 100% water to 30% water: 70% acetonitrile (both containing 0.1% trifluoroacetic acid.

Workup

  1. customThe reaction was partitioned between 300 mL ethyl acetate and 300 mL pH 4.5 citric acid solution (buffered with NaOH)
  2. dry with materialthe ethyl acetate dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-092b8fc87c8a46ce8e758553629d6e3b
Source dataset
uspto-grants-2002_12
Patent number
US06492516B1

Reaction notes

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