| Identification | More | [Name]
6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone | [CAS]
36725-28-7 | [Synonyms]
6-(4-AMINOPHENYL)-4,5-DIHYDRO-5-METHYL-3(2H)PYRIDAZINONE
6-(4-AMINO-PHENYL)-5-METHYL-4,5-DIHYDRO-2H-PYRIDAZIN-3-ONE
LEVOSIMENDAN DAZINONES INTERMEDIATES
(R)-6-(4-AMINOPHENYL)-4,5-DIHYDRO-5-METHYLPYRIDAZIN-3(2H)ONE
6-(4-Aminophenyl)-5-methylpyridazin-3(2H)one
6-(4''-AMINOPHENYL)-4,5-DIHYDRO-5-METHYLPYRIDAZIN-3-ONE
ICI 109,081
6-(p-Aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone
6-(4-AMINOPHENYL)-5-METHYLPYRIDAZIN-3(2H)ONE, 98+%
1,4-Dihydro-4-methyl-3-(4-aminophenyl)pyridazine-6(5H)-one
6-(p-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone | [Molecular Formula]
C11H13N3O | [MDL Number]
MFCD01692712 | [Molecular Weight]
203.24 | [MOL File]
36725-28-7.mol |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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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