2-Pyridinamine, 5-iodo- → HCID 69203579, compound

HRID 751271Notes

Reaction equation

HRID 751271 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][CH:6]=O)[CH3:2].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][N:11]=1.C(#N)C.C(O)C>C(=O)(O)[O-].[Na+]>[CH2:1]([O:3][C:4]([C:5]1[N:11]2[CH:12]=[C:13]([I:16])[CH:14]=[CH:15][C:10]2=[N:9][CH:6]=1)=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 885792-Pyridinamine, 5-iodo-HCID 110298063-Oxo-propionic acid ethyl esterHCID 21984225Acetonitrile ethanol

Product 1

HCID 69203579HCID 69203579, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Reflux a solution of 3-oxo-propionic acid ethyl ester (J. Med. Chem. 2001, 44(12), 1193-2003; 3.4 g, 23.7 mmol) and 2-amino-5-iodopyridine in 1:1 acetonitrile/ethanol (100 mL) overnight. Dilute with saturated aqueous sodium bicarbonate, extract into dichloromethane (4×100 mL), combine organics, and concentrate. Flash chromatography using appropriate ethyl acetate/hexane mixtures gives 3.7 g (78%) of the subtitled compound as an off-white solid. ES+ m/e 316.7 (M+1).

Workup

  1. extractionextract into dichloromethane (4×100 mL)
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-4143c9f7f2824ec8934c2853a1f0931c
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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