Potassium Phosphate, Tribasic → HCID 66576810, compound

HRID 523588Notes

Reaction equation

HRID 523588 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: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: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 68899458HCID 68899458, compound

Product 1

HCID 66576810HCID 66576810, compoundYield 14.3%

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, 0.5076 mmol) was reacted with 1-(3-bromo-pyridin-4-yl)-cyclobutanol (I-33c: 127 mg, 0.5583 mmol) copper iodide (9.6 mg, 0.0507 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (21 mg, 0.1522 mmol), potassium phosphate (269 mg, 1.269 mmol) and 1,4-dioxane (3 mL) to afford crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3), followed by preparative HPLC afforded 25 mg of pure product (14% yield)

Workup

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

Sources & evidence

ORD record
ord-61a7fd2dd1a94940afd99162f81de08b
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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