HCID 131726433, compound → HCID 91055345, compound

HRID 1350098Notes

Reaction equation

HRID 1350098 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([Br:28])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8]([CH:10]1[CH2:15][NH:14][CH2:13][CH2:12][N:11]1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[CH3:23])=[O:9]>C(=O)([O-])O.[Na+]>[Br:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([Br:28])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8]([CH:10]1[CH2:15][NH:14][CH2:13][CH2:12][N:11]1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[CH3:23])=[O:9]

Participants

3

Reactant 1

HCID 131726433HCID 131726433, compound

Product 1

HCID 91055345HCID 91055345, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

The compound of EXAMPLE 10 (120 mg) was dissolved in a 5% sodium hydrogen carbonate solution (10 mL) and extracted with AcOEt (15 mL). The organic layer was dried and concentrated in vacuo to give 1-(4-fluoro-2-methyl-phenyl)-piperazine-2-carboxylic acid (3,5-dibromo-benzyl)-methylamide (94 mg). This material was separated into enantiomers by HPLC (conditions: column Chiralcel OD 25 cm×20 mm, mobile phase n-hexane/EtOH 80:20, flow 7 mL/min; detector DAD, λ=225 nm). Thus, 1-(4-fluoro-2-methyl-phenyl)-piperazine-2-carboxylic acid (3,5-dibromo-benzyl)-methylamide was obtained as:

Workup

  1. extractionextracted with AcOEt (15 mL)
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed1787c91600485b87286601a8e9c9a3
Source dataset
uspto-grants-2007_05
Patent number
US07214680B2

Reaction notes

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