6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone Chemical Properties

Melting point:

194.0 to 198.0 °C

Density 

1.30±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

13.90±0.60(Predicted)

color 

Pale Yellow to Brown

InChI

InChI=1S/C11H13N3O/c1-7-6-10(15)13-14-11(7)8-2-4-9(12)5-3-8/h2-5,7H,6,12H2,1H3,(H,13,15)

InChIKey

NWUOGOISBQCNKQ-UHFFFAOYSA-N

SMILES

C1(=O)NN=C(C2=CC=C(N)C=C2)C(C)C1

CAS DataBase Reference

36725-28-7(CAS DataBase Reference)

Safety Information

HS Code 

2933.99.8290

6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone Usage And Synthesis

Uses

AMDP3 (4-Aminophenyl)-4-methyl-4,5-dihydro-1H-pyridazin-6-one) acts as a cardiac troponin effecter, resulting in activation of cardiac muscle contractions. It’s an analogue to Levosimendan (L378000), positive inotropic agent with vasodilating activity.

Synthesis

General procedure for the synthesis of 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone from 4-(4-aminophenyl)-3-methyl-4-oxobutanoic acid hydrochloride: hydrazine hydrate (1.40 mL, 28.7 mmol) was added to an ethanolic solution of intermediate 3 (2.69 g, 11.04 mmol, dissolved in 70 mL of ethanol), the The reaction mixture was heated to reflux at 80 °C for 18 hours. After completion of the reaction, the mixture was concentrated in vacuum and the residue was ground with ethyl acetate to afford the target product Intermediate 7 in 1.46 g yield, 65%. The product was characterized by 1H NMR (300 MHz, CD3OD): δ [ppm] = 1.13 (d, 3H), 2.33 (d, 1H), 2.66 (dd, 1H), 3.28-3.40 (m, 1H), 6.68 (d, 2H), 7.56 (d, 2H). analysis by UPLC-MS (Method 3) showed a retention time R = 0.47 min and 100% purity. m/z (M + H)+ = 204 as measured by MS (ESIpos).

References

[1] Arzneimittel-Forschung/Drug Research, 2007, vol. 57, # 10, p. 641 - 646
[2] Journal of Heterocyclic Chemistry, 1988, vol. 25, # 6, p. 1689 - 1695
[3] Patent: WO2018/86703, 2018, A1. Location in patent: Page/Page column 204

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