28682-70-4

Usage

Uses

Used in Pharmaceutical Synthesis:
4,5-Pyridazinediamine(9CI) is used as a reagent for the synthesis of various pharmaceuticals. Its aminated structure allows for the creation of a wide range of compounds with potential therapeutic applications.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 25, p. 831, 1988 DOI: 10.1002/jhet.5570250326

Synthetic route

5-amino-4-nitropyridazine (118617-12-2) → pyridazine-4,5-diamine (28682-70-4)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol for 0.5h;	57%

4-amino-3,6-dichloro-5-nitropyridazine (28682-68-0) → pyridazine-4,5-diamine (28682-70-4)

Conditions	Yield
Stage #1: 4-amino-3,6-dichloro-5-nitropyridazine With 5%-palladium/activated carbon; hydrogen In methanol at 25℃; under 2585.81 Torr; Stage #2: With potassium carbonate In methanol; dichloromethane at 20℃;	9 g

3,6-bis[4-(diphenylamino)phenyl]-9,10-phenanthrenequinone (1415100-79-6) + pyridazine-4,5-diamine (28682-70-4) → C54H36N6

Conditions	Yield
With acetic acid Reflux;	82%

benzoic acid (65-85-0) + pyridazine-4,5-diamine (28682-70-4) → 2-phenyl-1H-imidazo[4,5-d]pyridazine (1081-28-3)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 25℃; for 18h;	56%

glyoxylic acid ethyl ester (924-44-7) + pyridazine-4,5-diamine (28682-70-4) → pyrazino[2,3-d]pyridazin-2(1H)-one (1620840-34-7)

Conditions	Yield
In ethanol at 80℃;	49.7%

S-methyl-2-methoxy-4-methyl-thiobenzoic acid morpholide + pyridazine-4,5-diamine (28682-70-4) → 2-(2-Methoxy-4-methyl-phenyl)-imidazo[4,5-d]pyridazine hydrochloride

1,1'-carbonyldiimidazole (530-62-1) + pyridazine-4,5-diamine (28682-70-4) → pyrazino[2,3-d]pyridazine-2,3(1H,4H)-dione (1558736-74-5)

Conditions	Yield
In N,N-dimethyl-formamide at 75℃; for 16h;

oxalic acid (144-62-7) + pyridazine-4,5-diamine (28682-70-4) → pyrazino[2,3-d]pyridazine-2,3(1H,4H)-dione hydrochloride

Conditions	Yield
With hydrogenchloride In water for 20h; Reflux;

Upstream product

• 28682-68-0 4-amino-3,6-dichloro-5-nitropyridazine 
• 118617-12-2 5-amino-4-nitropyridazine 

Downstream Products

• 1081-28-3 2-phenyl-1H-imidazo[4,5-d]pyridazine 

Relevant academic research and scientific papers

QUINOXALINONES AND DIHYDROQUINOXALINONES AS RESPIRATORY SYNCYTIAL VIRUS ANTIVIRAL AGENTS

Quinoxalinones and dihydroquinoxalinones having inhibitory activity on RSV replication and having the formula (I) including addition salts, and stereochemically isomeric forms thereof; compositions containing these compounds as active ingredient and processes for preparing these compounds and compositions.

Amination of 4-Nitro- and 4-Cyanopyridazines by Liquid Ammonia/Potassium Permanganate

4-Nitro-3-R1-6-R2-pyridazines (1) (a, R1 = R2 =2-pyridyl; b, R1 = H, R2 = phenyl; c, R1 = H, R2 = p-methoxyphenyl; d, R1 = R2 = H) are aminated by liquid ammonia/potassium permanganate to the corresponding 5-amino-4-nitropyridazines 3a-d.The 4-cyano-3-R1-6-R2-pyridazines 4a,b are only aminated in the presence of potassium amide in liquid ammonia/potassium permanganate to give the 5-amino-4-cyanopyridazines 6a,b.The 5-amino-4-nitropyridazines 3a,b,d are converted to the 4,5-diaminopyridazines 7a,b,d by reduction over a Pd/C catalyst.Reaction of7b with glyoxal leads to 5-phenylpyrazinopyridazine (8b).