1,3-Propanediamine → HCID 57718193, compound

HRID 1366821Notes

Reaction equation

HRID 1366821 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 (1 H, s, py); 6.77 (1 H, s, py); 4.50 (2 H, br s, NH2); 4.24 (2 H, t, OCH2); 1.72 (2 H, m, OCH2CH2); 1.32 (4 H, m, OCH2CH2CH2CH2CH3); 0.81 (3 H, 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-0b145ad523ed42d09a276ce2f8de7648
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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