Potassium Carbonate → HCID 89691256, compound

HRID 2203068Notes

Reaction equation

HRID 2203068 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]3[CH2:12][CH2:11]3)[N:7]([CH3:13])[C:6]=2[CH:14]=1.[O:15]=[C:16]1[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][NH:17]1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.O1CCOCC1>[CH:10]1([C:8]2[N:7]([CH3:13])[C:6]3[CH:14]=[C:2]([N:17]4[CH:18]=[CH:19][C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:21][C:16]4=[O:15])[CH:3]=[CH:4][C:5]=3[N:9]=2)[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 280755Methyl 2-oxo-1,2-dihydropyridine-4-carboxylateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 838254226-Bromo-2-cyclopropyl-1-methyl-1H-benzoimidazole

Product 1

HCID 89691256HCID 89691256, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-bromo-2-cyclopropyl-1-methyl-1H-benzimidazole (984 mg), methyl 2-oxo-1,2-dihydropyridine-4-carboxylate (600 mg), potassium carbonate (1.08 g) and dioxane (25 ml) were added CuI (298 mg) and trans-N,N′-dimethylcyclohexane-1,2-diamine (223 mg), and the mixture was heated at 80° C. for 12 h. The mixture was concentrated in vacuo, and diluted with DCM. The mixture was washed with brine, dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (MeOH/DCM) to give the title compound (800 mg) as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with DCM
  3. washThe mixture was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-67968faa58d04a4ebd9132bb3fd82085
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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