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[ CAS No. 5424-05-5 ] {[proInfo.proName]}

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Chemical Structure| 5424-05-5
Chemical Structure| 5424-05-5
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Product Details of [ 5424-05-5 ]

CAS No. :5424-05-5 MDL No. :MFCD00094018
Formula : C8H7N3 Boiling Point : -
Linear Structure Formula :- InChI Key :YOWAEZWWQFSEJD-UHFFFAOYSA-N
M.W : 145.16 Pubchem ID :224573
Synonyms :

Calculated chemistry of [ 5424-05-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.94
TPSA : 51.8 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.35
Log Po/w (XLOGP3) : 1.5
Log Po/w (WLOGP) : 1.22
Log Po/w (MLOGP) : 0.66
Log Po/w (SILICOS-IT) : 1.26
Consensus Log Po/w : 1.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.637 mg/ml ; 0.00439 mol/l
Class : Soluble
Log S (Ali) : -2.2
Solubility : 0.925 mg/ml ; 0.00637 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.95
Solubility : 0.164 mg/ml ; 0.00113 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 5424-05-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5424-05-5 ]

* 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 [ 5424-05-5 ]
  • Downstream synthetic route of [ 5424-05-5 ]

[ 5424-05-5 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 101101-68-2 ]
  • [ 5424-05-5 ]
YieldReaction ConditionsOperation in experiment
25% With ammonium formate In methanol at 20℃; for 48 h; A mixture of 2-benzylaminoquinoxaline (1.30 g, 5.50 mmol), ammonium formate (3.13 g, 49.7 mmol) and Pd-C (10percent Pd, 130 mg) in MeOH (60 mL) was stirred at . rt for 48 h. The mixture was filtered through Celite.(R)., concentrated and purified by chromatography to give the title compound (278 mg, 25percent) as an orange oil. 1H NMR (DMSO-J6, 400 MHz) δ 8.26 (s, IH), 7.74 (d, IH), 7.55-7.46 (m, 2H), 7.30 (ddd, IH), 6.95 (s, 2H).
Reference: [1] Patent: WO2007/51982, 2007, A1, . Location in patent: Page/Page column 39
  • 2
  • [ 1448-87-9 ]
  • [ 5424-05-5 ]
YieldReaction ConditionsOperation in experiment
5% With ammonia In methanol; hexane; dichloromethane Step 1:
To 2-chloroquinoxaline (1.0 g, 6 mmol) was added ammonia in methanol (8 mL of a 2M solution).
The reaction was sealed in a vial, heated to 80° C., and stirred for 12 hours.
The reaction was cooled to room temperature and concentrated under reduced pressure.
The residue was taken up in methylene chloride and filtered.
Hexane was added until a precipitate formed which was filtered and found to be the desired product (5percent yield).
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 12, p. 3773 - 3777[2] Angew. Chem., 2015, vol. 127, # 12, p. 3844 - 3848,5
[3] Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737
[4] Tetrahedron, 2010, vol. 66, # 34, p. 6958 - 6964
[5] Patent: US2003/69284, 2003, A1,
[6] Journal of the Chemical Society, 1945, p. 622,625
[7] Patent: US2537870, 1946, ,
  • 3
  • [ 34117-90-3 ]
  • [ 829-85-6 ]
  • [ 5424-05-5 ]
  • [ 1422239-76-6 ]
  • [ 4559-70-0 ]
  • [ 1101-41-3 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: at 130℃; for 2 h; Inert atmosphere; Schlenk technique
Stage #2: With potassium hydroxide In diethyl ether; water
Heating a mixture of 2a (495 mg, 2.75 mmol) and Ph2PH (0.48 mL, 2.76 mmol) in the presence of Pd(OAc)2 (0.8 mg, 0.13 molpercent) for 2 h at 130°C led to a viscous blue-green mass. Extraction of the soluble part with diethyl ether and NMR monitoring in C6D6 identified Ph2P-PPh2, Ph2PCl, 3a and an unknown phosphorus compound (31P signals at d 14.9, 82.2, 12.8 and 5.4 ppm, intensity ratio 84:12:2:2). The insoluble hydrochloride part, 615 mg blue-green powder, was treated with aqueous NaOH/Et2O. The ether phase was dried with Na2SO4 and the ether removed in vacuo to give a brownish-yellow viscous mass (220 mg) with a low content of 3a (relative 31P intensity ca. 20percent besides signals of Ph4P2, Ph2PHO and other P compounds). Purification under aerobic conditions by column chromatography on silica gel (ethyl acetate/hexane 95/5percent) and removal of solvent gave 180 mg (45percent) pale yellow solid 2-aminoquinoxaline. Mp: 156°C. 1H NMR (CDCl3) d: 5.03 (vbr s, 2H, NH2), 7.45 (td, 3J = 8.4, 7, 4J = 1.2 Hz, 1H, H-6), 7.61 (td, 3J = 8.4, 7, 4J = 1.2 Hz, 1H, H-7), 7.67 (dd, 3J = 8.4, 4J = 1.2 Hz, 1H, H-8), 7.92 (dd, 3J = 8.4, 4J = 1.2 Hz, 1H, H-5), 8.35 (s, 1H, H-3); these values are in good agreement with the reported data [17]. 13C NMR (CDCl3) d: 125.05 (CH-6), 125.88 (CH-8), 128.83 (CH-5), 137.43 (Cq-4a), 137.78 (CH-3), 130.29 (CH-7), 140.89 (Cq-8a), 151.97 (Cq-2). HRMS (ESI in MeOH): Calc. for C8H7N3 [M+H+] 146.0713; found: 146.0713.
Reference: [1] Polyhedron, 2013, vol. 50, # 1, p. 101 - 111
  • 4
  • [ 34117-90-3 ]
  • [ 829-85-6 ]
  • [ 5424-05-5 ]
  • [ 1422239-76-6 ]
Reference: [1] Polyhedron, 2013, vol. 50, # 1, p. 101 - 111
  • 5
  • [ 95-54-5 ]
  • [ 5424-05-5 ]
Reference: [1] Journal of the Chemical Society, 1945, p. 622,625
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 4955
[3] Journal of the American Chemical Society, 1951, vol. 73, p. 4955
[4] Patent: US2537870, 1946, ,
[5] Journal of the Chemical Society, 1945, p. 622,625
  • 6
  • [ 60093-60-9 ]
  • [ 5424-05-5 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 4955
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 4955
[3] Patent: US2650221, 1951, ,
[4] Patent: US2650221, 1951, ,
  • 7
  • [ 490-59-5 ]
  • [ 5424-05-5 ]
Reference: [1] Journal of the Chemical Society, 1956, p. 26,27
[2] Journal of the American Chemical Society, 1944, vol. 66, p. 1957
[3] Journal of the American Chemical Society, 1944, vol. 66, p. 1957
  • 8
  • [ 1196-57-2 ]
  • [ 5424-05-5 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 7, p. 1788 - 1791
  • 9
  • [ 85414-82-0 ]
  • [ 5424-05-5 ]
Reference: [1] Journal of the American Chemical Society, 1944, vol. 66, p. 1957
  • 10
  • [ 91-19-0 ]
  • [ 5424-05-5 ]
  • [ 6640-47-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1285 - 1287
  • 11
  • [ 2213-63-0 ]
  • [ 5424-05-5 ]
  • [ 1422239-76-6 ]
Reference: [1] Polyhedron, 2013, vol. 50, # 1, p. 101 - 111
  • 12
  • [ 1196-57-2 ]
  • [ 5424-05-5 ]
Reference: [1] Journal of the Chemical Society, 1945, p. 622,625
[2] Patent: US2537870, 1946, ,
  • 13
  • [ 7664-93-9 ]
  • [ 490-59-5 ]
  • [ 5424-05-5 ]
Reference: [1] Journal of the Chemical Society, 1956, p. 26,27
[2] Journal of the American Chemical Society, 1944, vol. 66, p. 1957
  • 14
  • [ 20254-76-6 ]
  • [ 5424-05-5 ]
Reference: [1] Journal of the Chemical Society, 1945, p. 622,625
  • 15
  • [ 23395-75-7 ]
  • [ 5424-05-5 ]
Reference: [1] Journal of the Chemical Society, 1945, p. 622,625
  • 16
  • [ 49679-45-0 ]
  • [ 5424-05-5 ]
Reference: [1] Journal of the Chemical Society, 1945, p. 622,625
  • 17
  • [ 36818-07-2 ]
  • [ 5424-05-5 ]
Reference: [1] Journal of the Chemical Society, 1945, p. 622,625
  • 18
  • [ 91-19-0 ]
  • [ 5424-05-5 ]
  • [ 6640-47-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1285 - 1287
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