1-Hydroxybenzotriazole → 2-(2,5-Dioxoimidazolidin-4-yl)-N-[2-(4'-fluoro-1,1'-biphenyl-4-yl)propyl]-acetamide

HRID 899348Notes

Reaction equation

HRID 899348 reaction equation
[NH:1]1[CH:7]([CH2:8][C:9]([OH:11])=O)[C:5](=[O:6])[NH:4][C:2]1=[O:3].C1C=CC2N(O)N=NC=2C=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]([CH3:38])[CH2:36][NH2:37])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1>CN1C(=O)CCC1>[O:3]=[C:2]1[NH:1][CH:7]([CH2:8][C:9]([NH:37][CH2:36][CH:35]([C:32]2[CH:33]=[CH:34][C:29]([C:26]3[CH:25]=[CH:24][C:23]([F:22])=[CH:28][CH:27]=3)=[CH:30][CH:31]=2)[CH3:38])=[O:11])[C:5](=[O:6])[NH:4]1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 95492Hydantoin-5-acetic acidHCID 203025312-(4'-Fluoro-biphenyl-4-yl)-propylamine

Product 1

HCID 100219942-(2,5-Dioxoimidazolidin-4-yl)-N-[2-(4'-fluoro-1,1'-biphenyl-4-yl)propyl]-acetamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent3×

Procedure

600μL of a 0.15M solution in NMP of 5-hydantoin acetic acid was mixed with 98 mg of polystyrene-bound caibodiimide resin (loading 1.28 mmol/g). 340 μL of a 0.3M solution of HOBT in NMP was added to the mixture and vortexed for 10 minutes before 200 μL of a 0.3M solution in NMP of 2-(4′-fluoro-biphenyl-4-yl)-propylamine was added. The reaction mixture was vortexed overnight at room temperature in a sealed vessel. Resin was removed by filtration and the solution was evaporated to dryness. The product was purified on semi prep-HPLC C18-column (H2O:CH3CN, 0.1% TFA buffer, gradient 10% to 95% CH3CN, 10 min).

Workup

  1. additionwas added
  2. customResin was removed by filtration
  3. customthe solution was evaporated to dryness
  4. customThe product was purified on semi prep-HPLC C18-column (H2O:CH3CN, 0.1% TFA buffer, gradient 10% to 95% CH3CN, 10 min)

Sources & evidence

ORD record
ord-bbf7915f8b0e486faab4b5500d76e570
Source dataset
uspto-grants-2008_04
Patent number
US07354940B2

Reaction notes

Loading…