Potassium Carbonate → 3-[3-(1-Cyclohexylazetidin-3-ylamino)-4-trifluoromethoxyphenyl]-5,5-dimethyl-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione

HRID 2356956Notes

Reaction equation

HRID 2356956 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[N:15]([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[C:14]2=[O:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].C(O)(=O)C(O)=O.CS(O[CH:40]1[CH2:43][N:42]([CH:44]2[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]2)[CH2:41]1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C>[CH:44]1([N:42]2[CH2:43][CH:40]([NH:1][C:2]3[CH:3]=[C:4]([N:13]4[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[N:15]([CH2:21][C:22]5[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=5)[C:14]4=[O:28])[CH:5]=[CH:6][C:7]=3[O:8][C:9]([F:10])([F:11])[F:12])[CH2:41]2)[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 231103083-(3-Amino-4-trifluoromethoxyphenyl)5,5-dimethyl-1-pyridin-4-ylmethylimidazolidine-2,4-dioneHCID 866172261-Cyclohexylazetidin-3-yl methanesulphonate oxalate2×

Product 1

HCID 669158113-[3-(1-Cyclohexylazetidin-3-ylamino)-4-trifluoromethoxyphenyl]-5,5-dimethyl-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

300 mg (0.76 mmol) of 3-(3-amino-4-trifluoromethoxyphenyl)5,5-dimethyl-1-pyridin-4-ylmethylimidazolidine-2,4-dione were dissolved in 15 ml of ethyl acetate, admixed with 492 mg (1.52 mmol) of 1-cyclohexylazetidin-3-yl methanesulphonate oxalate and 631 mg (4.56 mmol) of K2CO3, and heated under reflux for 4 h. To complete the reaction, a further 49 mg (0.15 mmol) of 1-cyclohexylazetidin-3-yl methanesulphonate oxalate and 63 mg (0.46 mmol) of K2CO3 were added, and the mixture was stirred under reflux once again for 2 h. Subsequently, the mixture was concentrated and the residue purified by flash chromatography (150 g of silica gel/95:5 CH2C12:CH3OH).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 h
  3. customthe reaction
  4. temperatureunder reflux once again for 2 h
  5. concentrationSubsequently, the mixture was concentrated
  6. customthe residue purified by flash chromatography (150 g of silica gel/95:5 CH2C12:CH3OH)

Sources & evidence

ORD record
ord-0c29a66265eb4608b6f0e8e20dca3194
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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