Potassium Phosphate, Tribasic → HCID 66576816, compound

HRID 523605Notes

Reaction equation

HRID 523605 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.Br[C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([F:24])=[CH:19][N:18]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][N:12]([C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([F:24])=[CH:19][N:18]=3)[C:11]2=[O:15])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 38574302-bromo-5-fluoro-4-methylpyridineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 66576816HCID 66576816, compoundYield 39.21%

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 100 mg, 0.492 mmol) was reacted with 2-bromo-5-fluoro-4-methylpyridine (102 mg, 0.541 mmol) 1,4-dioxane (5 mL), copper iodide (9 mg, 0.0492 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (21 mg, 0.147 mmol) and potassium phosphate (313 mg, 1.47 mmol) to afford the crude product. Purification by column chromatography on silica gel (80% ethyl acetate in hexane) afforded 60 mg of the product (39.21% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (80% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ac4e628265e34eae8a44ec19d3ff5dfd
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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