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[ CAS No. 5469-70-5 ] {[proInfo.proName]}

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Chemical Structure| 5469-70-5
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Product Details of [ 5469-70-5 ]

CAS No. :5469-70-5 MDL No. :MFCD01529869
Formula : C4H5N3 Boiling Point : -
Linear Structure Formula :- InChI Key :LETVJWLLIMJADE-UHFFFAOYSA-N
M.W : 95.10 Pubchem ID :230373
Synonyms :

Calculated chemistry of [ 5469-70-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 26.44
TPSA : 51.8 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.8
Log Po/w (XLOGP3) : -1.21
Log Po/w (WLOGP) : 0.07
Log Po/w (MLOGP) : -0.32
Log Po/w (SILICOS-IT) : 0.38
Consensus Log Po/w : -0.06

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.3
Solubility : 47.5 mg/ml ; 0.499 mol/l
Class : Very soluble
Log S (Ali) : 0.62
Solubility : 393.0 mg/ml ; 4.14 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.21
Solubility : 5.93 mg/ml ; 0.0624 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

Safety of [ 5469-70-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5469-70-5 ]

* 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 [ 5469-70-5 ]
  • Downstream synthetic route of [ 5469-70-5 ]

[ 5469-70-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 5469-69-2 ]
  • [ 5469-70-5 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydroxide; hydrogen In tetrahydrofuran; water at 20℃; for 48 h; Example 147; 4-(3-Phenyl-1,2,4-thiadiazol-5-yl)-N-pyridazine-1-carboxamide; (1) Pyridazine-3-amine; A mixture of 6-chloropyridazine-3-amine (5.00 g, 38.6 mmol), tetrahydrofuran (240 ml), sodium hydroxide (8.00 g, 200 mmol), water (32 ml) and 10percent palladium-carbon (500 mg) was stirred under a hydrogen atmosphere at room temperature for 2 days, insolubles were filtered off and the filtrate was concentrated. The residue was dissolved in methanol (100 ml), insolubles were filtered off and the filtrate was concentrated to obtain the desired product as a solid quantitatively. 1H-NMR (DMSO-d6) δ; 2.51 (2H, br s), 6.46 - 6.49 (1H, m), 6.93 - 6.97 (1H, m), 8.06 - 8.08 (1H, m).
100% With palladium on activated charcoal; hydrogen; sodium hydroxide In ethanol at 20℃; for 20 h; To a solution of 2 (875 mg, 6.76 mmol) and sodium hydroxide(304 mg, 6.76 mmol) in absolute ethanol (30 mL) stirred underargon was added Pd/C (131 mg, 1.23 mmol). The mixture was thenstirred at room temperature under hydrogen atmosphere and reaction progress was followed by TLC monitoring. After 20 h, themixture was filtered through a celite pad and the filtrate wasevaporated under reduced pressure. The crude product waswashed with Et2O to give compound 30 (700 mg, 100percent) as a palepink solid.Mp 164.1 C. 1H NMR (300 MHz, CDCl3) d 8.58 (dd, 1H, J 4.5,1.5 Hz, H6), 7.23 (dd, 1H, J 9.0, 4.5 Hz, H5), 6.83 (dd, 1H, J 9.0,1.5 Hz, H4), 5.18 (bs, 2H, NH2). 13C NMR (75 MHz, CDCl3) d 159.5,144.1, 128.2, 114.6.
99.5% With hydrogen; sodium hydroxide In ethanol at 20℃; for 18 h; Example 23Synthesis of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridazinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.A mixture of 0.063 g (0.486 mmol) of 6-chloro-3-pyridazinamine (J. Med. Chem. 2006, 49, 4409-4424), 0.022 g (0.55 mmol) of NaOH, and 0.045 g of 10percent Pd/C in ethanol (15 mL) was stirred under an atmosphere of hydrogen for 18 hrs. After filtration through celite, the solvent was concentrated to give 0.046 g (99.5percent yield) of 3-aminopyridazine: 1H NMR (DMSO-d6) δ8.39 (dd, J=4.4, 1.2 Hz, 1H), 7.21 (dd, J=8.8, 4.4 Hz, 1H), 6.74 (dd, J=9.2, 1.6 Hz, 1H), 6.26 (br s, 2H).To a solution of 0.159 g (1.67 mmol) of 3-aminopyridazine in THF (3 mL) at 0° C. was added 0.93 mL of NaHMDS (2 M solution in THF), and the mixture was stirred for 15 min. A solution of 0.317 g (0.84 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-1H-benzimidazole in THF (6 mL) was added and the resulting mixture was stirred for 1 hr at RT. After neutralization with acetic acid, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed sequentially with water and aq. NH3, dried and concentrated. Chromatography on alumina, eluting first with hexane-EtOAc (8:2) then with CH2Cl2/EtOAc (2:1) to CH2Cl2/EtOAc (1:1) gave a white powder. Recrystallization from ethanol/CH2Cl2 gave 0.065 g (18percent yield) of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridazinyl)-1,3,5-triazin-2-amine: mp 271-273° C.; 1H NMR (DMSO-d6) δ11.16 (br s, 1H), 8.98 (dd, J=4.7, 1.4 Hz, 1H), 8.67 (d, J=8.0 Hz, 1H), 8.61 (d, JHF=8.4 Hz, 1H), 8.08 (t, JHF=52.8 Hz, 1H), 7.86 (dd, J=7.7, 0.7 Hz, 1H), 7.73 (dd, J=9.1, 4.7 Hz, 1H), 7.53-7.43 (m, 2H), 3.86 (s, 4H), 3.75 (s, 4H); Anal. Calcd. for C19H17F2N9O: C, 53.65; H, 4.1; N, 29.6. Found: C, 53.7; H, 4.2; N, 29.5percent.
78% With hydrogen; triethylamine In ethanol for 1.9 h; Example 39; Synthesis of 4-(3-(5-cyclopropylpyridin-2-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide; Step 1; Pyridazin-3-amine; To a solution of 6-chloropyridazin-3-amine (19.2 g, 148 mmol) in EtOH (500 mL) was added 10percent Pd catalyst on 1940 carbon (unreduced, 55percent water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NH4Cl. The organic layer was concentrated to give the title compound as a white solid (11 g, 78percent yield). MS (APCI 10V) AP+1 96.2.
78% With hydrogen In ethanol for 1.9 h; Synthesis of Phenyl pyridazin-3-ylcarbamate; To a solution of 3-amino-6-chloropyridazine (19.2 g, 148 mmol; CAS No.5469-69-2) in EtOH (500 mL) was added 10percent Pd catalyst on 1940 carbon (unreduced, 55percent water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NH4Cl. The organic layer was concentrated to give pyridazin-3-amine as a white solid (11 g, 78percent yield). MS (APCI 10V) AP+1 96.2. To a suspension of pyridazin-3-amine (5 g, 50 mmol) in THF (50 mL) and CH3CN (70 mL) was added pyridine (5.10 mL, 63.1 mmol) followed by phenyl chloroformate (6.95 mL, 55.2 mmol) slowly. The reaction was stirred overnight. The reaction was filtered to remove the precipitate. The filtrate was concentrated and then taken up in CH2Cl2 which was washed with water. The organic layer was dried using SPE phase separators and concentrated. The residue was purified by silica gel column chromatography (0-5percent MeOH/CH2Cl2). An undesired side product eluted first followed by the title compound which was concentrated to give a white solid (7.5 g, 70percent yield). MS (APCI 10V) AP+1 216.12; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.20-7.24 (m, 2H) 7.25-7.28 (m, 1H) 7.39-7.44 (m, 2H) 7.64-7.69 (m, 1H) 8.05 (dd, 1H) 8.94 (dd, 1H) 11.34 (s, 1H).
78% With hydrogen; triethylamine In ethanol; water for 1.9 h; Phenyl pyridazin-3-ylcarbamateTo a solution of 3-amino-6-chloropyridazine (19.2 g,148 mmol; CASNo. 5469-69-2) in EtOH (500 mL) was added 10percent Pd catalyst on 1940 carbon (unreduced, 55percent water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NH4CI. The organic layer was concentrated to give pyridazin-3-amine as a white solid (11 g, 78percent yield). MS (APCI 10V) AP+ 1 96.2. To a suspension of pyridazin-3-amine (5 g, 50 mmol) in THF (50 mL) and CH3CN (70 mL) was added pyridine (5.10 mL, 63.1 mmol) followed by phenyl chloroformate (6.95 mL, 55.2 mmol) slowly. The reaction was stirred overnight. The reaction was filtered to remove the precipitate. The filtrate was concentrated and then taken up in CH2CI2 which was then washed with water. The organic layer was dried using SPE phase separators and concentrated. The residue was purified by silica gel column chromatography (0-5percent MeOH/CH2CI2). An undesired side product eluted first followed by the title compound which was concentrated to give a white solid (7.5 g, 70percent yield). MS (APCI 10V) AP+1 216.12; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.20 - 7.24 (m, 2 H) 7.25 - 7.28 (m, 1 H) 7.39 - 7.44 (m, 2 H) 7.64 - 7.69 (m, 1 H) 8.05 (dd, 1 H) 8.94 (dd, 1 H) 11.34 (s, 1 H).
78% With hydrogen; triethylamine In ethanol; water for 1.9 h; To a solution of 3-amino-6-chloropyridazine (19.2 g,148 mmol; CASNo. 5469-69-2) in EtOH (500 mL) was added 10percent Pd catalyst on 1940 carbon (unreduced, 55percent water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NH4CI. The organic layer was concentrated to give pyridazin-3-amine as a white <n="27"/>solid (11 g, 78percent yield). MS (APCI 10V) AP+1 96.2. To a suspension of pyridazin-3-amine (5 g, 50 mmol) in THF (50 mL) and CH3CN (70 mL) was added pyridine (5.10 mL, 63.1 mmol) followed by phenyl chloroformate (6,95 mL, 55.2 mmol) slowly. The reaction was stirred overnight. The reaction was filtered to remove the precipitate. The filtrate was concentrated and then taken up in CH2CI2 which was washed with water. The organic layer was dried using SPE phase separators and concentrated. The residue was purified by silica gel column chromatography (0-5percent MeOH/CH2CI2). An undesired side product eluted first followed by the title compound which was concentrated to give a white solid (7.5 g, 70percent yield). MS (APCI 10V) AP+1 216.12; 1H NMR (400 MHz1 DMSO-d6) δ ppm 7.20 - 7.24 (m, 2 H) 7.25 - 7.28 (m, 1 H) 7.39 - 7.44 (m, 2 H) 7.64 - 7.69 (m, 1 H) 8.05 (dd, 1 H) 8.94 (dd, 1 H) 11.34 (s, 1 H).
78% With hydrogen; triethylamine In ethanol; water for 1.9 h; To a solution of 3-amino-6-chloropyridazine (19.2 g,148 mmol; CASNo. 5469-69-2) in EtOH (500 mL) was added 10percent Pd catalyst on 1940 carbon (unreduced, 55percent water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NH4CI. The organic layer was concentrated to give pyridazin-3-amine as a white solid (11 g, 78percent yield). MS (APCI 10V) AP+1 96.2. To a suspension of pyridazin-3-amine (5 g, 50 mmol) in THF (50 mL) and CH3CN (70 mL) was added pyridine (5.10 mL, 63.1 mmol) followed by phenyl chloroformate (6.95 mL, 55.2 mmol) slowly. The reaction was stirred overnight. The reaction was filtered to remove the precipitate. The filtrate was concentrated and then taken up in CH2CI2 which was washed with water. The organic layer was dried using SPE phase separators and concentrated. The residue was <n="31"/>purified by silica gel column chromatography (0-5percent MeOH/CH2CI2). An undesired side product eluted first followed by the title compound which was concentrated to give a white solid (7.5 g, 70percent yield). MS (APCI 10V) AP+1 216.12; 1H NMR (400 MHz, DMSOd6) δ ppm 7.20 - 7.24 (m, 2 H) 7.25 - 7.28 (m, 1 H) 7.39 - 7.44 (m, 2 H) 7.64 - 7.69 (m, 1 H) 8.05 (dd, 1 H) 8.94 (dd, 1 H) 11.34 (s, 1 H).

Reference: [1] Patent: EP1813606, 2007, A1, . Location in patent: Page/Page column 82
[2] European Journal of Medicinal Chemistry, 2015, vol. 105, p. 80 - 105
[3] Patent: US2011/9405, 2011, A1, . Location in patent: Page/Page column 48
[4] Tetrahedron, 1993, vol. 49, # 3, p. 599 - 606
[5] Patent: US2008/261941, 2008, A1, . Location in patent: Page/Page column 29
[6] Patent: US2010/113465, 2010, A1, . Location in patent: Page/Page column 17
[7] Patent: WO2010/58318, 2010, A1, . Location in patent: Page/Page column 30
[8] Patent: WO2009/127946, 2009, A1, . Location in patent: Page/Page column 25; 26
[9] Patent: WO2009/127948, 2009, A1, . Location in patent: Page/Page column 29; 30
[10] Journal of the American Chemical Society, 1954, vol. 76, p. 3225
[11] Patent: WO2012/7006, 2012, A1, . Location in patent: Page/Page column 46
[12] Patent: WO2012/40230, 2012, A1, . Location in patent: Page/Page column 81-82
[13] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5957 - 5964
[14] Patent: WO2013/12915, 2013, A1, . Location in patent: Paragraph 00933
[15] Patent: WO2013/142269, 2013, A1, . Location in patent: Paragraph 0511; 0512
[16] Patent: WO2009/127944, 2009, A1, . Location in patent: Page/Page column 29
[17] Patent: WO2009/127949, 2009, A1, . Location in patent: Page/Page column 29
  • 2
  • [ 1120-95-2 ]
  • [ 5469-70-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 3, p. 350 - 361
[2] Chemische Berichte, 1948, vol. 81, p. 1,10
[3] Patent: DE859621, 1957, ,
[4] Journal of the Chemical Society, 1948, p. 2191,2194
[5] Journal of the American Chemical Society, 1942, vol. 64, p. 2902
[6] Journal of the Chemical Society, 1948, p. 2191,2194
[7] Journal of the American Chemical Society, 1942, vol. 64, p. 2902
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  • [ 20744-39-2 ]
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Reference: [1] Patent: US4735650, 1988, A,
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  • [ 88497-27-2 ]
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Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 3225
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  • [ 40972-16-5 ]
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Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1259 - 1261
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  • [ 17114-78-2 ]
  • [ 5469-70-5 ]
  • [ 106358-48-9 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 6 - 10[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 1, p. 9 - 14
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  • [ 5469-70-5 ]
  • [ 107-20-0 ]
  • [ 766-55-2 ]
Reference: [1] Patent: CN105218551, 2016, A, . Location in patent: Paragraph 0024
[2] Patent: CN105218550, 2016, A, . Location in patent: Paragraph 0025
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