Potassium Phosphate, Tribasic → HCID 49872654, compound

HRID 80240Notes

Reaction equation

HRID 80240 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[C:18]([CH3:24])=[CH:19][C:20]([F:23])=[N:21][CH:22]=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[CH:22]=[N:21][C:20]([F:23])=[CH:19][C:18]=4[CH3:24])[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 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 231570625-Bromo-2-fluoro-4-methylpyridineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 49872654HCID 49872654, compoundYield 28.9%

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-2-fluoro-4-methyl-pyridine (130 mg, 0.6849 mmol), 1,4-dioxane (5 mL), copper iodide (13 mg, 0.06849 mmol), trans -N,N′-dimethyl-cyclohexane-1,2-diamine (32.3 mL, 0.2054 mmol) and potassium phosphate (362.9 mg, 1.7122 mmol) to afford the crude product. Purification by column chromatography on silica gel (60% ethylacetate in hexane) afforded 65 mg of the product (28.9% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (60% ethylacetate in hexane)

Sources & evidence

ORD record
ord-8e906dbd9bec47c38b41ecd0dd948c8d
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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