Potassium Acetate → 1-{3-[(dipyridin-3-ylamino)methyl]pyridine-2-yl}-3-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 563950Notes

Reaction equation

HRID 563950 reaction equation
Cl[C:2]1[C:7]([CH2:8][N:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:22][N:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[NH:25][C:24]1=[O:32].C([O-])(=O)C.[K+]>N1C=CC=CC=1.C([O-])(O)=O.[Na+].[Cu]>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([N:9]([CH2:8][C:7]2[C:2]([N:25]3[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[N:23]([CH3:22])[C:24]3=[O:32])=[N:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:11]=1

Participants

7

Reactant 3

HCID 517044Potassium AcetateHCID 5905401-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-oneHCID 59138879N-[(2-chloropyridin-3-yl)methyl]-N-pyridin-3-ylpyridin-3-amine

Product 1

HCID 591388821-{3-[(dipyridin-3-ylamino)methyl]pyridine-2-yl}-3-methyl-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 1049PyridineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of N-[(2-chloropyridin-3-yl)methyl]-N-pyridin-3-ylpyridin-3-amine (59 mg, 020 mmol) and 1-methyl-2-benzimidazolinone (45 mg, 0.30 mmol) in dry pyridine (1 mL) was added potassium acetate (51 mg, 0.512 mmol), cuprous chloride (11.6 mg, 0.117 mmol), and copper powder (31 mg, 0.487 mmol). This mixture was sealed and heated at 120 C for 4 days. The cooled reaction was diluted with NaHCO3 solution and the product extracted into methylene chloride. This solution was dried over anhydrous sodium sulfate, filtered, and the solvent evaporated This residue was subjected to chromatography on silica gel eluting with a 20-100% acetone/hexane gradient to give the title compound after trituration with diethyl ether as a white solid.

Workup

  1. customThis mixture was sealed
  2. temperatureheated at 120 C for 4 days
  3. customThe cooled reaction
  4. extractionthe product extracted into methylene chloride
  5. dry with materialThis solution was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated This residue

Sources & evidence

ORD record
ord-eb8cac8cc76448aeb5351125ce8b130c
Source dataset
uspto-grants-2011_11
Patent number
US08067607B2

Reaction notes

Loading…