Potassium Phosphate, Tribasic → 3-[2-Oxo-3-(3-trifluoromethyl-phenyl)-imidazolidin-1-yl]-isonicotinic acid ethyl ester

HRID 523596Notes

Reaction equation

HRID 523596 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][CH:8]=1.[CH2:17]([O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1Br)[CH3:18].CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH2:17]([O:19][C:20](=[O:28])[C:21]1[CH:22]=[CH:23][N:24]=[CH:25][C:26]=1[N:11]1[CH2:12][CH2:13][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=2)[C:10]1=[O:14])[CH3:18]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 14781091-[3-(Trifluoromethyl)phenyl]-2-imidazolidinoneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 15141565Ethyl 3-bromoisonicotinate

Product 1

HCID 709841223-[2-Oxo-3-(3-trifluoromethyl-phenyl)-imidazolidin-1-yl]-isonicotinic acid ethyl esterYield 85%

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: 200 mg, 0.869 mmol) was reacted with 3-bromo-isonicotinic acid ethyl ester (239 mg, 1.042 mmol), copper iodide (16.5 mg, 0.869 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (37.01 mg, 0.26 mmol), potassium phosphate (460.5 mg, 2.172 mmol) and 1,4-dioxane (5 mL) to afford crude product. Purification by column chromatography on silica gel (60% ethyl acetate in hexane) afforded 280 mg of pure product (85% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford crude product
  3. customPurification by column chromatography on silica gel (60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d9c615c071b241a99d8129c516d01130
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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