Potassium Carbonate → methyl 5-[(4S)-2-oxo-3-(2-oxo-2-{[3-(trifluoromethyl)phenyl]amino]ethyl)-4-(propan-2-yl)imidazolidin-1-yl}pyridine-2-carboxylate

HRID 2401287Notes

Reaction equation

HRID 2401287 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C@H:11]([CH:13]([CH3:15])[CH3:14])[N:10]([CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[O:18])[C:9]2=[O:30])=[CH:4][CH:3]=1.[C:31](=[O:34])([O-])[O-:32].[K+].[K+].[C:37](=O)([O-])O.[Na+]>CN(C=O)C.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:30]=[C:9]1[N:10]([CH2:16][C:17](=[O:18])[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[C@@H:11]([CH:13]([CH3:15])[CH3:14])[CH2:12][N:8]1[C:5]1[CH:4]=[CH:3][C:2]([C:31]([O:32][CH3:37])=[O:34])=[N:7][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86705191HCID 86705191, compound

Product 1

HCID 86705194methyl 5-[(4S)-2-oxo-3-(2-oxo-2-{[3-(trifluoromethyl)phenyl]amino]ethyl)-4-(propan-2-yl)imidazolidin-1-yl}pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 19794673N,N-dimethylformamide ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2-[(5S)-3-(6-bromopyridin-3-yl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide (100 mg), potassium carbonate (43 mg), and Pd(PPh3)4 (24 mg) in DMF/ethanol (2:1, 2.1 mL) was stirred under atmosphere of carbon monoxide gas at 80° C. for 1.5 hr. Saturated aqueous sodium hydrogen carbonate solution was added thereto, the mixture was washed with ethyl acetate, and the organic layer was washed with water and brine. After concentration under reduced pressure, the residue was purified by preparative HPLC to afford methyl 5-[(4S)-2-oxo-3-(2-oxo-2-{[3-(trifluoromethyl)phenyl]amino]ethyl)-4-(propan-2-yl)imidazolidin-1-yl}pyridine-2-carboxylate (50 mg).

Workup

  1. washthe mixture was washed with ethyl acetate
  2. washthe organic layer was washed with water and brine
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-33a956c87018456d8287f13888362968
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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