3-Bromopyridine → 1-Benzothiazol-6-yl-4,4-dimethyl-3-pyridin-3-yl-imidazolidin-2-one

HRID 80215Notes

Reaction equation

HRID 80215 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]3=[O:17])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][C:13]([CH3:15])([CH3:16])[N:12]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[C:11]3=[O:17])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 122863-BromopyridineHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 596361661-Benzothiazol-6-yl-4,4-dimethyl-imidazolidin-2-one

Product 1

HCID 498729301-Benzothiazol-6-yl-4,4-dimethyl-3-pyridin-3-yl-imidazolidin-2-oneYield 11.45%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as described in example 14, 1-benzothiazol-6-yl-4,4-dimethyl-imidazolidin-2-one (I-164b: 100 mg, 0.4048 mmol) was reacted with 3-bromo-pyridine (83 mg, 0.525 mmol), 1,4-dioxane (10 mL), copper iodide (7 mg, 0.036 mmol), trans-1,2-diamino cyclohexane (17 mg, 0.119 mmol) and potassium phosphate (214 mg, 1.009 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in CHCl3) afforded 15 mg of the product (11.45% yield).

Workup

  1. customthe same reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1% MeOH in CHCl3)

Sources & evidence

ORD record
ord-a1b4e2bb9232496f86833446bc1afce1
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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