Potassium Carbonate → HCID 86645372, compound

HRID 1972286Notes

Reaction equation

HRID 1972286 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[CH2:11][N:10]([CH2:23][CH2:24][C:25]#[N:26])[C:9]2=[O:27])=[CH:4][CH:3]=1.Cl.[NH2:29][OH:30].C([O-])([O-])=O.[K+].[K+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=3)[CH2:11][N:10]([CH2:23][CH2:24][C:25](=[N:29][OH:30])[NH2:26])[C:9]2=[O:27])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 68705969HCID 68705969, compound

Product 1

HCID 86645372HCID 86645372, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (S)-3-(3-(4-chlorophenyl)-2-oxo-4-(3-(trifluoromethyl)-phenyl)imidazolidin-1-yl)propanenitrile (97 mg, 0.25 mmol), hydroxylamine hydrogen chloride (85.5 mg, 1.23 mmol), K2CO3 (187 mg, 1.35 mmol) and anhydrous ethanol (4 mL) are refluxed for 2 days. The solvent is removed under vacuum. The residue is taken into ethyl acetate, washed with sat. NaHCO3 and brine. The organic phase is dried by Mg2SO4. The solvent is removed under vacuum to afford crude (S)-3-(3-(4-chlorophenyl)-2-oxo-4-(3-(trifluoromethyl)phenyl)imidazolidin-1-yl)-N′-hydroxy-propanimidamide which is used directly in the next step without further purification. HPLC-MS calculated for C19H19ClF3N4O2 (M+H+) 427.1, found 427.1.

Workup

  1. temperatureare refluxed for 2 days
  2. customThe solvent is removed under vacuum
  3. washwashed with sat. NaHCO3 and brine
  4. dry with materialThe organic phase is dried by Mg2SO4
  5. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-ae68f0344684483296f19dd1b33cd925
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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