Potassium Phosphate, Tribasic → Usre45173, 188A

HRID 80254Notes

Reaction equation

HRID 80254 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][NH:12][C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:17]1[N:21]([CH3:22])[CH:20]=[N:19][CH:18]=1.CN[C@@H]1CCCC[C@H]1NC.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][CH2:13][N:12]([C:17]4[N:21]([CH3:22])[CH:20]=[N:19][CH:18]=4)[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 15152585-Bromo-1-methyl-1H-imidazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 59636242Usre45173, 188AYield 41.64%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-Benzothiazol-6-yl-imidazolidin-2-one (I-84b: 150 mg, 0.6849 mmol) was reacted with 5-bromo-1-methyl-1H-imidazole (121.3 mg, 0.753 mmol), 1,4-dioxane (5 mL), copper iodide (12.99 mg, 0.0684 mmol), trans N,N′-dimethyl-cyclohexane-1,2-diamine (29.176 mg, 0.205 mmol) and potassium phosphate (435.01 mg, 2.05 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 85 mg of the product (41.64% yield).

Workup

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

Sources & evidence

ORD record
ord-325d1c6e2f0942079eda21b5971c056b
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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