2-Imidazolidinone → 1-(4-Cyclopropylpyridin-3-yl)-3-(5-fluoro-3-methylbenzo[b]thiophen-6-yl)imidazolidin-2-one

HRID 523577Notes

Reaction equation

HRID 523577 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].Br[C:8]1[C:9]([F:18])=[CH:10][C:11]2[C:15]([CH3:16])=[CH:14][S:13][C:12]=2[CH:17]=1.CN[C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[NH:27][CH3:28].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOC[CH2:38]1>[Cu](I)I>[CH:25]1([C:24]2[CH:23]=[CH:22][N:27]=[CH:28][C:38]=2[N:1]2[CH2:5][CH2:4][N:3]([C:8]3[C:9]([F:18])=[CH:10][C:11]4[C:15]([CH3:16])=[CH:14][S:13][C:12]=4[CH:17]=3)[C:2]2=[O:6])[CH2:26][CH2:21]1

Participants

7

Reactant 5

HCID 84532-ImidazolidinoneHCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 709819996-Bromo-5-fluoro-3-methylbenzo[b]thiophene

Product 1

HCID 665767331-(4-Cyclopropylpyridin-3-yl)-3-(5-fluoro-3-methylbenzo[b]thiophen-6-yl)imidazolidin-2-oneYield 22%

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 4-cyclopropyl-pyridin-3-yl)-imidazolidin-2-one (I-1d: 150 mg, 0.7389 mmol) was reacted with 6-bromo-5-fluoro-3-methyl-benzo[b]thiophene (I-29b: 216 mg, 0.8866 mmol), 1,4-dioxane (5 mL), copper iodide (14.07 mg, 0.0738 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (10.4 mg, 0.0.0738 mmol) and potassium phosphate (469.9 mg, 2.2167 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in chloroform), followed by preparative HPLC afforded 62 mg of the product (22% yield).

Workup

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

Sources & evidence

ORD record
ord-f01f2a88c137400685b94a9bb409fbcf
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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