2-Pyridinamine, N-methyl- → HCID 66627607, compound

HRID 1471281Notes

Reaction equation

HRID 1471281 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[H-].[Na+].Cl[CH2:12][C:13]1[N:17]([CH3:18])[C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[N:14]=1>O1CCCC1>[CH3:1][N:2]([CH2:12][C:13]1[N:17]([CH3:18])[C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[N:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 207272-Pyridinamine, N-methyl-HCID 24758Sodium hydrideHCID 2480442-(Chloromethyl)-1-methylbenzimidazole

Product 1

HCID 66627607HCID 66627607, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flask were added 0.6 g 2-(methylamino)pyridine and 20 ml tetrahydrofuran, and the mixture was cooled to 5 C. To this mixture were added 0.26 g of 60% sodium hydride in mineral oil in small portions, and after stirring at 5-10 C for ten minutes, 1.0 g of 2-(chloromethyl)-1-methyl-1H-benzimidazole was added. The reaction mixture was heated to 45 C for 16 hours, then cooled to 22 C and quenched with 40 ml water. The product was extracted with 40 ml ethyl acetate and following removal of the solvent, the product was purified by silica gel chromatography using 63% ethyl acetate, 25% hexane and 12% methanol resulting in 0.55 g of a yellow solid.

Workup

  1. temperaturethe mixture was cooled to 5 C
  2. temperatureThe reaction mixture was heated to 45 C for 16 hours
  3. temperaturecooled to 22 C
  4. customquenched with 40 ml water
  5. extractionThe product was extracted with 40 ml ethyl acetate
  6. customremoval of the solvent
  7. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0ba213d67ba24409ba1b6f45a87de5bc
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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