2-Aminopyridine → HCID 21939938, compound

HRID 1242872Notes

Reaction equation

HRID 1242872 reaction equation
[N:1]1([CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]4[CH:29]=[CH:28][C:24]([C:25]([O-:27])=O)=[CH:23][CH:22]=4)[CH:15]=3)[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)(C)C(Cl)=O.[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C1COCC1.C(N(CC)CC)C>[N:1]1([CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]4[CH:22]=[CH:23][C:24]([C:25]([NH:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=5)=[O:27])=[CH:28][CH:29]=4)[CH:15]=3)[CH2:10]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 104392-AminopyridineHCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 21939875HCID 21939875, compound

Product 1

HCID 21939938HCID 21939938, compoundYield 8.4%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.11 ml) was added to THF suspension (6 ml) of 4-[[2-(2-piperidinoethyl)-6-tetraliny]oxymethyl]benzoate (300 mg). Trimethylacetyl chloride (0.095 ml) was added dropwise to the obtained suspension under ice-cooling, which was stirred for 30 minutes. The temperature of the reaction mixture was raised to room temperature, which was stirred for 1 hour. THF solution (1.0 ml) of 2-aminopyridine (110 mg) was added dropwise to the reaction mixture under ice-cooling, which was stirred for 1 hour. Then the reaction mixture was stirred at room temperature for 6 hours, and at 60° C. for 12 hours, which was refluxed with heating for 6 hours. Saturated sodium bicarbonate solution was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using alumina column chromatography (development solvent: THF), and recrystallized (ethyl acetate-IPE) to give the titled compound (30 mg).

Workup

  1. temperaturecooling
  2. stirringwhich was stirred for 1 hour
  3. temperaturecooling
  4. stirringwhich was stirred for 1 hour
  5. stirringThen the reaction mixture was stirred at room temperature for 6 hours
  6. waitat 60° C. for 12 hours
  7. temperaturewhich was refluxed
  8. temperaturewith heating for 6 hours
  9. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  10. customdried
  11. concentrationconcentrated
  12. customThe residue was purified
  13. customrecrystallized (ethyl acetate-IPE)

Sources & evidence

ORD record
ord-7ef5cea24cd94910a518d4f93d6cdedc
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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