Potassium Phosphate, Tribasic → HCID 66576811, compound

HRID 572435Notes

Reaction equation

HRID 572435 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])[CH:5]=[CH:4][N:3]=1.Br[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[C:21]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22]1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][N:10]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[C:21]3([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22]3)[C:9]2=[O:13])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 20636580HCID 20636580, compoundHCID 70982889HCID 70982889, compound

Product 1

HCID 66576811HCID 66576811, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(2-chloro-pyridin-4-yl)imidazolidin-2-one (I-33b: 100 mg, 0.5 mmol) was reacted with 1-(3-bromo-pyridin-4-yl)-cyclopentanol (I-34a: 135 mg, 0.558 mmol), copper iodide (9.6 mg, 0.05 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (21.62 mg, 0.15 mmol), potassium phosphate (322.87 mg, 1.52 mmol) and 1,4-dioxane (5 mL) to yield the crude product. Purification by preparative HPLC afforded 20 mg of the product (11% yield).

Workup

  1. customreagents and reaction conditions
  2. customto yield the crude product
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-cd8dddf0d9b4415584c088fdc953492c
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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