6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
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6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
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CAS No:
36725-28-7
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Formula:
C11H13N3O
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Chemical Name:
6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
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Synonyms:
LEVOSIMENDAN DAZINONES INTERMEDIATES;6-(4-AMINOPHENYL)-4,5-DIHYDRO-5-METHYL-3(2H)PYRIDAZINONE;6-(4-AMINO-PHENYL)-5-METHYL-4,5-DIHYDRO-2H-PYRIDAZIN-3-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
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CAS No:
6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone Basic Attributes
203.24
203.105865
Pale Yellow to Brown
2933.99.8290
Characteristics
67.5
0.8
1.30±0.1 g/cm3(Predicted)
194.0 to 198.0 °C
1.653
13.90±0.60(Predicted)
Keep in dark place,Sealed in dry,Room Temperature
6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone Use and Manufacturing
To a solution of Intermediate 3, 2.69 g (11.04 minol), in ethanol, 70 mL, was added hydrazine hydrate, 1.40 mL (28.7 minol), the reaction was heated at 8000 for 18 hours. The reaction wasconcentrated under vacuum and triturated with ethyl acetate to give the desired product Intermediate 7, 1.46 g (65percent).1H NMR (300 MHz, CD3OD): 6 [ppm] = 1.13 (d, 3H), 2.33 (d, IH), 2.66 (dd, IH), 3.28-3.40 (m, IH), 6.68 (d, 2H), 7.56 (d, 2H).UPLC-MS (Method 3): R = 0.47 min., 100percent. MS (ESIpos): m/z (M÷H) 204.EXAMPLE 8 (+) and (-)-6-(4-Aminophenyl)-5-methyl-4, 5-dihydro-3(2H)-pyridazinone Racemic The later fractions from the first column were enriched (-)-enantiomer (approximately 75% enrichment). This (0.05 g) was subjected to high pressure liquid chromatography (Jobin-Yvon system) over a column of ionically bound (S)-N-(3, 5-dinitrobenzoyl)phenylglycine on 25-40 mum gamma-aminopropyl silanized silica (55 g) eluding with dichloromethane/methanol (199:1). The appropriate fractions were combined with fractions from another run and re-chromatographed through the same column. This afforded (+)-enantiomer (0.035 g) in approximately 100% enantiomeric excess. The selected column fractions were evaporated, triturated with diethyl ether, filtered and the resultant solid washed with diethyl ether and dried at 80 C. for 18 hours to give (+)-(-)-EXAMPLE 10 (-)-(-)-(-)-(-)-EXAMPLE 3 (-)-EXAMPLE 4 (-)-EXAMPLE 5 (-)-EXAMPLE 6 (-)-EXAMPLE 7 (-)-EXAMPLE 8 (-)-(-)-A sample of racemic
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.
Computed Properties
Molecular Weight:203.24
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:203.105862047
Monoisotopic Mass:203.105862047
Topological Polar Surface Area:67.5
Heavy Atom Count:15
Complexity:280
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
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