Potassium Phosphate, Tribasic → HCID 66576730, compound

HRID 523564Notes

Reaction equation

HRID 523564 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:18]=[C:19]([F:26])[C:20]2[CH:24]=[CH:23][S:22][C:21]=2[CH:25]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[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:18]=[C:19]([F:26])[C:20]4[CH:24]=[CH:23][S:22][C:21]=4[CH:25]=3)[C:11]2=[O:15])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-oneHCID 709821066-Bromo-4-fluoro-1-benzothiophene

Product 1

HCID 66576730HCID 66576730, compoundYield 26%

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: 120 mg, 0.591 mmol) was reacted with 6-bromo-4-fluoro-benzo[b]thiophene (I-26d: 163.6 mg, 0.738 mmol), copper iodide (11.2 mg, 0.059 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (8.9 mg, 0.0591 mmol), potassium phosphate (375.9 mg, 1.7 mmol) and 1,4-dioxane (5 mL). Purification by column chromatography on silica gel (0.3% methanol in CHCl3) afforded 51.2 mg of the product (26% yield).

Workup

  1. customreagents and reaction conditions
  2. customPurification by column chromatography on silica gel (0.3% methanol in CHCl3)

Sources & evidence

ORD record
ord-48f205be8ea34112b0fb5fc1fc5f5b50
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

Loading…