Potassium Phosphate, Tribasic → 4-Cyclopropyl-3-(2-oxo-3-(2-(trifluoromethyl) pyridin-4-yl)imidazolidin-1-yl) pyridine 1-oxide

HRID 572456Notes

Reaction equation

HRID 572456 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])[CH:6]=[CH:7]C=1.[CH:17]1([C:20]2[CH:25]=[CH:24][N+:23]([O-:26])=[CH:22][C:21]=2I)[CH2:19][CH2:18]1.C[NH:29][C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH:17]1([C:20]2[CH:25]=[CH:24][N+:23]([O-:26])=[CH:22][C:21]=2[N:11]2[CH2:12][CH2:13][N:9]([C:5]3[CH:6]=[CH:7][N:29]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=3)[C:10]2=[O:14])[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 14781091-[3-(Trifluoromethyl)phenyl]-2-imidazolidinoneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 709832464-Cyclopropyl-3-iodopyridine 1-oxide

Product 1

HCID 710079694-Cyclopropyl-3-(2-oxo-3-(2-(trifluoromethyl) pyridin-4-yl)imidazolidin-1-yl) pyridine 1-oxideYield 713.7%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(3-trifluoromethyl-phenyl)-imidazolidin-2-one (I-36b: 60 mg, 0.259 mmol) was reacted with 4-cyclopropyl-3-iodopyridine 1-oxide (I-50a: 81 mg, 0.31 mmol), copper iodide (5 mg, 0.025 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (4 mg, 0.025 mmol), potassium phosphate (165 mg, 0.77 mmol) and 1,4-dioxane (5 mL) to afford crude product. Purification by column chromatography on silica gel (1.5% methanol in chloroform) afforded 65 mg of pure product (71.4% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford crude product
  3. customPurification by column chromatography on silica gel (1.5% methanol in chloroform)

Sources & evidence

ORD record
ord-224978ac428043a68eaceed3566ccc86
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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