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[ CAS No. 19064-65-4 ] {[proInfo.proName]}

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Chemical Structure| 19064-65-4
Chemical Structure| 19064-65-4
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Product Details of [ 19064-65-4 ]

CAS No. :19064-65-4 MDL No. :MFCD00234098
Formula : C5H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :ASFHDLDAWYTMJS-UHFFFAOYSA-N
M.W : 110.11 Pubchem ID :292493
Synonyms :

Calculated chemistry of [ 19064-65-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 28.52
TPSA : 35.01 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.57
Log Po/w (XLOGP3) : 0.08
Log Po/w (WLOGP) : 0.49
Log Po/w (MLOGP) : 0.09
Log Po/w (SILICOS-IT) : 0.94
Consensus Log Po/w : 0.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.06
Solubility : 9.54 mg/ml ; 0.0867 mol/l
Class : Very soluble
Log S (Ali) : -0.37
Solubility : 47.0 mg/ml ; 0.427 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.72
Solubility : 2.11 mg/ml ; 0.0192 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 19064-65-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 19064-65-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 19064-65-4 ]
  • Downstream synthetic route of [ 19064-65-4 ]

[ 19064-65-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 1722-10-7 ]
  • [ 19064-65-4 ]
YieldReaction ConditionsOperation in experiment
88% With ammonium formate In methanol at 20℃; for 0.5 h; 3-Methoxypyridazine3-chloro-6-methoxypyridazine (3.60 g, 24.90 mmol), 10percent Pd/C (1.590 g, 1.49 mmol) and ammonium formate (3.14 g, 49.81 mmol) were stirred in methanol (20 mL) at room temperature for thirty minutes. The reaction mixture was filtered through Celite to get rid of Pd/C, and the filtrate was evaporated to dry. The residue was dissolved in methylene chloride, washed with water once, dried through MgSO4, filtrated and evaporated to dry to give a brown liquid as the title compound (2.41 g, 88percent yield, 95percent purity). The crude material was used for next step without further purification. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 8.83 (dd, J=4.4, 1.3 Hz, 1 H) 7.35 (dd, J=8.9, 4.4 Hz, 1 H) 6.97 (dd, J=8.9, 1.3 Hz, 1 H) 4.14 (s, 3 H. MS APCI, m/z=152 (M+ACN+H). HPLC 0.43 min.
87% With hydrogen In methanol A mixture of 3-chloro-6-methoxypyridazine (1.0 g, 6.9 mmol) in methanol (50 mL) with 33percent palladium on carbon (100 mg) was hydrogenated under 45 psi overnight. The catalyst was removed by filtration through a pad of Celite. The filtrate was concentrated and dissolved in EtOAc. The solution was washed several times with a saturated NaHCO3 solution and brine, dried over MgSO4, concentrated to give a crude product, which was purified on a silica gel column eluting with EtOAc/n-hexane (1:2) to give 3-methoxypyridazine as a pale yellow solid (662 mg, 87percent). 1H NMR (300 MHz, CDCl3): δ 4.14 (s, 3H), 6.98 (dd, J=1.2, 9.0 Hz, 1H), 7.36 (dd, J=4.5, 8.7 Hz, 1H), 8.84 (dd, J=1.2, 4.5 Hz, 1H).
86% With ammonium formate In methanol at 50℃; for 1 h; Inert atmosphere PREPARATION 8; 3- ethoxy-4-(tributylstannyl)pyridazine a) 3-MethoxypyridazinePalladium on carbon (10percent, 0.1 g) and ammonium formate (2.1 g, 33.3 mmol) were added to a stirred solution of 3-chloro-6-methoxypyridazine (2.5 g, 26.43 mmol) in methanol (10 mL) and the resulting mixture was stirred at 50 °C for 1 hour. The reaction was cooled down, filtered through Celite.(R). under nitrogen atmosphere eluting with methanol and the filtrate was evaporated to dryness. The crude product was diluted with dichloromethane and washed with water. The organic layer was dried over magnesium sulphate and the solvent removed under reduced pressure to yield the title compound (1.55 g, 86percent) as a pale yellow oil.1H-NMR δ (300 MHz, CDCI3): 4.16 (s, 3H), 7.00 (dd, 1 H), 7.38 (dd, 1 H), 8.82 -8.87 (m, 1H).
86% With ammonium formate In methanol at 50℃; for 1 h; PREPARATION 8 ;3-Methoxy-4-(tributylstannyl)pyridazine a) 3-Methoxypyridazine Palladium on carbon (10percent, 0.1 g) and ammonium formate (2.1 g, 33.3 mmol) were added to a stirred solution of 3-chloro-6-methoxypyridazine (2.5 g, 26.43 mmol) in methanol (10 mL) and the resulting mixture was stirred at 50 C for 1 hour. The reaction was cooled down, filtered through Celite.(R). under nitrogen atmosphere eluting with methanol and the filtrate was evaporated to dryness. The crude product was diluted with dichloromethane and washed with water. The organic layer was dried over magnesium sulphate and the solvent removed under reduced pressure to yield the title compound (1.55 g, 86percent) as a pale yellow oil. 1H-NMR δ (300 MHz, CDCl3): 4.16 (s, 3H), 7.00 (dd, 1H), 7.38 (dd, 1H), 8.82 - 8.87 (m, 1H).
71% With hydrogen In methanol at 20℃; for 17 h; 1)
3-Methoxypyridazine
In a hydrogen atmosphere, at room temperature, 10percent palladium-carbon (wet. 3.12 g) was added to a solution of 3-chloro-6-methoxypyridazine (30.0 g) in methanol (200 mL), and the mixture was stirred for 17 hours.
The reaction mixture was subjected to filtration, and the solvent of the filtrate was evaporated under reduced pressure.
The residue was purified through silica gel column chromatography (ethyl acetate), to thereby give 3-methoxypyridazine as an oily product (16.3 g, 71percent).
1H-NMR(400MHz,CDCl3)δ:4.14(3H,s), 6.98(1H,d,J=9.0Hz), 7.37 (1H, dd, J=9.0,4.4Hz), 8.84 (1H, d, J=9.4Hz).

Reference: [1] Patent: US2008/318943, 2008, A1, . Location in patent: Page/Page column 74
[2] Patent: US2006/148801, 2006, A1, . Location in patent: Page/Page column 13
[3] Patent: WO2012/69202, 2012, A1, . Location in patent: Page/Page column 50-51
[4] Patent: EP2463289, 2012, A1, . Location in patent: Page/Page column 20
[5] Patent: EP1762568, 2007, A1, . Location in patent: Page/Page column 51-52
[6] Helvetica Chimica Acta, 1956, vol. 39, p. 1755,1762
[7] Yakugaku Zasshi, 1954, vol. 74, p. 1195,1197[8] Chem.Abstr., 1955, p. 14768
  • 2
  • [ 141-30-0 ]
  • [ 124-41-4 ]
  • [ 19064-65-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 19, p. 4716 - 4730
  • 3
  • [ 1120-95-2 ]
  • [ 124-41-4 ]
  • [ 19064-65-4 ]
Reference: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 60
  • 4
  • [ 19064-65-4 ]
  • [ 1722-10-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1959, vol. 7, p. 938,940
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