1,3-Propanediamine → HCID 57718193, compound

HRID 1984573Notes

Reaction equation

HRID 1984573 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9](Br)=[CH:8][N:7]=[C:6]([NH2:11])[CH:5]=1.[I-:13].[Na+].NC[CH2:17][CH2:18]N.C(O[CH2:24][CH3:25])(=O)C>C(O)CCCC.[Cu](I)I>[CH2:1]([O:2][C:3](=[O:12])[C:4]1[C:9]([I:13])=[CH:8][N:7]=[C:6]([NH2:11])[CH:5]=1)[CH2:17][CH2:18][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 4281,3-PropanediamineHCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 25307230Methyl 2-amino-5-bromoisonicotinate

Product 1

HCID 57718193HCID 57718193, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 62761-PentanolSolvent

Procedure

2-amino-5-bromo-isonicotinic acid methyl ester (1.79 g, 7.75 mmol) was added to a stirred mixture of copper iodide (145 mg, 0.76 mmol), sodium iodide (2.36 g, 15.73 mmol) and 1,3-diaminopropane (0.13 ml, 1.55 mmol) in n-pentanol (20 ml) and heated to reflux overnight. The reaction was cooled to room temperature, ethyl acetate (100 ml) added and washed with NaHCO3 solution (50 ml) and brine (50 ml) before being dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography using ethyl acetate 1/4 hexane as eluent to afford 2-amino-5-iodo-isonicotinic acid pentyl ester as a yellow solid (1.51 g, 58%). 1H NMR (CDCl3): 8.36 (1H, s, py); 6.77 (1H, s, py); 4.50 (2H, br s, NH2); 4.24 (2H, t, OCH2); 1.72 (2H, m, OCH2CH2); 1.32 (4H, m, OCH2CH2CH2CH2CH3); 0.81 (3H, t, CH2CH3).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. washwashed with NaHCO3 solution (50 ml) and brine (50 ml)
  4. dry with materialbefore being dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-841c0deeed134f70a93dd59be0f96402
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

Loading…