Potassium Phosphate, Tribasic → HCID 66576648, compound

HRID 523547Notes

Reaction equation

HRID 523547 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:26]=[CH:25][C:20]2[S:21][C:22]([Cl:24])=[CH:23][C:19]=2[CH:18]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:24][C:22]1[S:21][C:20]2[CH:25]=[CH:26][C:17]([N:12]3[CH2:13][CH2:14][N:10]([C:5]4[CH:6]=[N:7][CH:8]=[CH:9][C:4]=4[CH:1]4[CH2:3][CH2:2]4)[C:11]3=[O:15])=[CH:18][C:19]=2[CH:23]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 185424665-Bromo-2-chlorobenzo[b]thiopheneHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 66576648HCID 66576648, compoundYield 33%

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: 100 mg, 0.491 mmol) was reacted with 5-bromo-2-chloro-benzo[b]thiophene- (134.6 mg, 0.541 mmol), copper iodide (9.3 mg, 0.049 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (7.0 mg, 0.0491 mmol), potassium phosphate (260.9 mg, 1.23 mmol) and 1,4-dioxane (5 mL to yield the crude product. Purification by column chromatography on silica gel (1.5% methanol in DCM), afforded 60.0 mg of the product (33% yield)

Workup

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

Sources & evidence

ORD record
ord-6ccbebd4cbe44d158ea8c5c7a1838e4b
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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