HCID 86705174, compound → HCID 86705173, compound

HRID 2401273Notes

Reaction equation

HRID 2401273 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH2:10][C@H:9]([CH:11]([CH3:13])[CH3:12])[N:8]([CH2:14][C:15]([NH:17][C:18]2[CH:19]=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=2)=[O:16])[C:7]1=[O:28]>FC(F)(F)C(O)=O>[O:28]=[C:7]1[NH:6][CH2:10][C@H:9]([CH:11]([CH3:12])[CH3:13])[N:8]1[CH2:14][C:15]([NH:17][C:18]1[CH:19]=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=1)=[O:16]

Participants

3

Reactant 1

HCID 86705174HCID 86705174, compound

Product 1

HCID 86705173HCID 86705173, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (20 mL) was added to 2-[(5S)-3-(2,4-dimethoxybenzyl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[6-(trifluoromethyl)pyridin-3-yl]acetamide (900 mg), and the mixture was stirred at room temperature for 3 hr. The solvent was distilled off under reduced pressure, and saturated sodium hydrogen carbonate was added thereto, followed by extraction with chloroform. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate) to afford the title compound (310 mg).

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and saturated sodium hydrogen carbonate
  2. additionwas added
  3. extractionfollowed by extraction with chloroform
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f0f6f06a0a054852a15832f726f468e0
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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