Potassium Phosphate, Tribasic → 1-(2-Chloro-6-(trifluoromethyl)pyridin-4-yl)-3-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one

HRID 523598Notes

Reaction equation

HRID 523598 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:22]=[C:21](I)[CH:20]=[C:19]([C:24]([F:27])([F:26])[F:25])[N:18]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:16][C:17]1[CH:22]=[C:21]([N:12]2[CH2:13][CH2:14][N:10]([C:5]3[CH:6]=[N:7][CH:8]=[CH:9][C:4]=3[CH:1]3[CH2:3][CH2:2]3)[C:11]2=[O:15])[CH:20]=[C:19]([C:24]([F:25])([F:26])[F:27])[N:18]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 108597852-Chloro-4-iodo-6-(trifluoromethyl)pyridineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 665769721-(2-Chloro-6-(trifluoromethyl)pyridin-4-yl)-3-(4-cyclopropylpyridin-3-yl)imidazolidin-2-oneYield 10.6%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 110 mg, 0.5412 mmol) was reacted with 2-chloro-4-iodo-6-(trifluoromethyl)pyridine (200 mg, 0.6494 mmol), 1,4-dioxane (5 mL), copper iodide (10 mg, 0.0541 mmol), trans-N1,N2-dimethylcyclohexane-1,2-diamine (23 mg, 0.1623 mmol) and potassium phosphate (345 mg, 1.6236 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.5% methanol in CHCl3), followed by prep HPLC afforded 22 mg of the product (10% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1.5% methanol in CHCl3)

Sources & evidence

ORD record
ord-e565501d3cf8420895a9c84aa1860ca3
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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