Triethylamine → N-[6-amino-pyridin-3-yl]-hexanamide

HRID 1670698Notes

Reaction equation

HRID 1670698 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][N:11]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[NH2:9][C:10]1[N:11]=[CH:12][C:13]([NH:16][C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 203142,5-PyridinediamineHCID 67340Hexanoyl chloride

Product 1

HCID 57767023N-[6-amino-pyridin-3-yl]-hexanamideYield 65.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Hexanoyl chloride (1.1 equiv., 10.08 mmol, 1.36 g) was added dropwise to a cooled (0° C.) suspension of 2,5-diaminopyridine (I13) (1.0 equiv., 9.16 mmol, 1.00 g) and triethylamine (1.1 equiv., 10.08 mmol, 1.02 g) in chloroform (100 ml). The reaction mixture was stirred at room temperature for 2 h. The solvent was evaporated under reduced pressure, and the residue was brought on a filter and successively washed with saturated NaHCO3 solution, water and isopropyl ether. The crude product was further purified by column chromatography (dichloromethane/methanol 95:5; Rf=0.3) to give N-[6-amino-pyridin-3-yl]-hexanamide (I14) (1.24 g, yield=65%). 1H NMR (6, DMSO-D6): 0.87 (3H, t, J=6.9), 1.23-1.33 (4H, m), 1.53-1.60 (2H, m), 2.22 (2H, t, J=7.5 Hz), 5.67 (2H, s), 6.39 (1H, d, J=8.8 Hz), 7.54 (1H, dd, J=8.8, 2.6 Hz), 8.05 (1H, d, J=2.5 Hz), 9.53 (1H, s)

Workup

  1. temperaturea cooled
  2. customThe solvent was evaporated under reduced pressure
  3. filtrationa filter
  4. washsuccessively washed with saturated NaHCO3 solution, water and isopropyl ether
  5. customThe crude product was further purified by column chromatography (dichloromethane/methanol 95:5; Rf=0.3)

Sources & evidence

ORD record
ord-1178a8438e2f4d6a97d4cc27b1a2ae35
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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