3-Aminopyridine → HCID 18472357, compound

HRID 1387824Notes

Reaction equation

HRID 1387824 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)=[CH:17][CH:18]=3)[CH:13]=2)=[O:11])=[CH:5][CH:4]=1.[NH2:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1.C(=O)([O-])O.[Na+]>C1COCC1>[CH3:28][C:25]1[CH:26]=[CH:27][C:22]([C:16]2[CH:15]=[C:14]3[C:19]([CH2:20][CH2:21][C:12]([C:10]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([CH2:2][NH:29][C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)=[CH:8][CH:7]=4)=[O:11])=[CH:13]3)=[CH:18][CH:17]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 100093-AminopyridineHCID 516892Sodium BicarbonateHCID 18472361N-[4-(chloromethyl)phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide

Product 1

HCID 18472357HCID 18472357, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (7 ml) was dissolved N-[4-(chloromethyl)-phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide (150 mg), and to the mixture was added 3-aminopyridine (109 mg). The mixture was refluxed for 45 hours. The reaction mixture was cooled to room temperature, and to the mixture was added 5% sodium hydrogen carbonate solution (50 ml). The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=3/1) and recrystallized from ethyl acetate-hexane to give 7-(4-methylphenyl)-N-[4-[N-(3-pyridyl)aminomethyl]phenyl]-3,4-dihydronaphthalene-2-carboxamide (Compound 47) (14 mg) as colorless crystals.

Workup

  1. temperatureThe mixture was refluxed for 45 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified with column chromatography (ethyl acetate/hexane=3/1)
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ffd5de27af8c4199aa335e6049c52698
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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