ChemicalBook CAS DataBase List 3,4-Diaminopyridine

3,4-Diaminopyridine synthesis

9synthesis methods

Product Name:3,4-Diaminopyridine
CAS Number:54-96-6
Molecular formula:C5H7N3
Molecular Weight:109.13

Amifampridine is used as a drug, predominantly in the treatment of a number of rare muscle diseases. The phosphate salt of amifampridine is a more stable formulation that does not require refrigeration. In the United States, amifampridine is under investigation for the treatment of Lambert-Eaton myasthenic syndrome (LEMS). Amifampridine is also used to treat many of the congenital myasthenic syndromes, particularly those with defects in choline acetyltransferase, downstream kinase 7, and those where any kind of defect causes "fast channel" behaviour of the acetylcholine receptor Synthetic Description Reference: Bakke, J. M.; Riha, J. Synthesis of 3,4-diaminopyridine and imidazo[4,5-c]pyridines by nitration of 4-(acylamino)pyridines. Journal of Heterocyclic Chemistry. Volume 36. Issue 5. Pages 1143-1145. Journal. (1999) Synthetic Description Reference: Campbell, J. B.; Greene, J. M.; Lavagnino, E. R.; Gardner, D. N.; Pike, A. J.; Snoddy, J.; Taylor, E. C. New methods for preparing 2,3- and 3,4-diaminopyridines. Journal of Heterocyclic Chemistry. Volume 23. Issue 3. Pages 669-72. Journal. (1986). Synthetic Description Reference: Lei, Xiaolong; Sun, Xiaoxia; Zhang, Peilin; Hu, Yu. The new synthesis of quinoxaline derivatives monomer. Advanced Materials Research (Durnten-Zurich, Switzerland). Volume 781-784. Issue Advances in Chemical Engineering III. Pages 567-570, 5 pp. Journal; Online Computer File. (2013). Synthetic Description Reference: Frohn, Mike; Viswanadhan, Vellarkad; Pickrell, Alexander J.; Golden, Jennifer E.; Muller, Kristine M.; Buerli, Roland W.; Biddlecome, Gloria; Yoder, Sean C.; Rogers, Norma; Dao, Jennifer H.; Hungate, Randall; Allen, Jennifer R. Structure-guided design of substituted aza-benzimidazoles as potent hypoxia inducible factor-1α prolyl hydroxylase-2 inhibitors. Bioorganic & Medicinal Chemistry Letters.Volume 18. Issue 18. Pages 5023-5026. Journal. (2008)

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

Reference: Bakke, J. M.; Riha, J. Synthesis of 3,4-diaminopyridine and imidazo[4,5-c]pyridines by nitration of 4-(acylamino)pyridines. Journal of Heterocyclic Chemistry. Volume 36. Issue 5. Pages 1143-1145. Journal. (1999)

1681-37-4 Synthesis

1681-37-4
343 suppliers
$5.00/1g

54-96-6
359 suppliers
$5.00/100mg

Yield:54-96-6 97%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in tetrahydrofuran at 10; under 760.051 Torr; for 24 h;

Steps:

1 Step 1 : synthesis of pyridine-3,4-diamine 8
The commercially available 3-nitropyridin-4-amine (50 g, 395 mmol) in the mixture of methanol (500 ml) and THF (500 ml) was hydrogenated with 10 % Pd/C (5 g) as a catalyst at 10°C (1 atm) for 24 h. After uptake of (3 eq), the catalyst was filtered off and the filtrate was evaporated. 38 g of the title intermediate 8 was obtained, (Yield 97 %).

References:

JANSSEN R&D IRELAND;TAHRI, Abdellah;JONCKERS, Tim Hugo Maria;RABOISSON, Pierre Jean-Marie Bernard;DEMIN, Samu?l Dominique WO2014/114776, 2014, A1 Location in patent:Page/Page column 25

FullText