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Chemical Structure| 15804-19-0
Chemical Structure| 15804-19-0
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Product Details of [ 15804-19-0 ]

CAS No. :15804-19-0 MDL No. :MFCD00006723
Formula : C8H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ABJFBJGGLJVMAQ-UHFFFAOYSA-N
M.W : 162.15 Pubchem ID :27491
Synonyms :

Calculated chemistry of [ 15804-19-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.19
TPSA : 65.72 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.75
Log Po/w (XLOGP3) : 0.2
Log Po/w (WLOGP) : 0.22
Log Po/w (MLOGP) : 0.6
Log Po/w (SILICOS-IT) : 2.22
Consensus Log Po/w : 0.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.59
Solubility : 4.19 mg/ml ; 0.0258 mol/l
Class : Very soluble
Log S (Ali) : -1.14
Solubility : 11.8 mg/ml ; 0.0726 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.13
Solubility : 0.12 mg/ml ; 0.000738 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 15804-19-0 ]

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

Application In Synthesis of [ 15804-19-0 ]

* 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 [ 15804-19-0 ]
  • Downstream synthetic route of [ 15804-19-0 ]

[ 15804-19-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 15804-19-0 ]
  • [ 34117-90-3 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[2] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[3] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
  • 2
  • [ 15804-19-0 ]
  • [ 6640-47-7 ]
Reference: [1] Helvetica Chimica Acta, 1994, vol. 77, # 6, p. 1549 - 1556
  • 3
  • [ 15804-19-0 ]
  • [ 2213-63-0 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With trichlorophosphate In N,N-dimethyl-formamide at 50℃; for 4 h;
Stage #2: With ammonia In waterCooling with ice
General procerure: A mixture of quinoxalin-2,3(1H,4H)-dione (1) [16] or compound 2 (40 mmol) and phosphours oxychloride (100 mmol) in dimethyl foramide (20 mL) was stirred at 50 °C for 4 h. The reaction mixture was added portion wise to ice/water and neutralized with ammonia solution 30percent. The formed precipitate was filtered off and purified on column chromatography by using petroleum ether (60-80): ethyl acetate (9:1) as an eluent.
80% for 5 h; Reflux A solution of compound 7 (30.84mmol, 5.0g) in phosphorus oxychloride (30mL) was reacted under refluxing condition for 5h, then the reaction was totally quenched by slowly pouring into cooled ammonia solution. The mixture was extracted with ethyl acetate (2×50mL), the combined organic phase was washed with brine (30mL) and dried over anhydrous MgSO4. After evaporated in vacuo, the crude residue was purified by silica gel flash chromatography (PE/EtOAc=10:1, v:v) to give 4.9g of corresponding product with 80percent yield. M.p. 149–150°C; ESI-MS m/z: 199.8 [M+H]+.
Reference: [1] Tetrahedron, 2008, vol. 64, # 22, p. 5410 - 5415
[2] ChemMedChem, 2012, vol. 7, # 5, p. 823 - 835
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 327 - 340
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1991, vol. 30, # 10, p. 936 - 940
[5] Helvetica Chimica Acta, 1994, vol. 77, # 6, p. 1549 - 1556
[6] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 771 - 777
[7] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1110 - 1112
[8] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 311 - 325
[9] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 7, p. 2260 - 2266
[10] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3689 - 3695
[11] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 20, p. 6433 - 6441
[12] Heterocycles, 2006, vol. 68, # 9, p. 1973 - 1979
[13] Journal of the Chemical Society, 1955, p. 1804,1806
[14] Patent: US2495202, 1945, ,
[15] Nippon Kagaku Zasshi, 1959, vol. 80, p. 945[16] Chem.Abstr., 1961, p. 4514
[17] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 1, p. 45 - 51
[18] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 12, p. 1371 - 1373
[19] Molecules, 2004, vol. 9, # 4, p. 223 - 231
[20] European Journal of Medicinal Chemistry, 2011, vol. 46, # 11, p. 5540 - 5548
[21] Heterocycles, 2012, vol. 86, # 2, p. 1583 - 1590
[22] Patent: CN103304584, 2016, B, . Location in patent: Paragraph 0017; 0018; 0025
[23] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 174 - 181
[24] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 117 - 134
[25] Patent: CN104529915, 2018, B, . Location in patent: Paragraph 0105; 0108; 0109
  • 4
  • [ 15804-19-0 ]
  • [ 2213-63-0 ]
YieldReaction ConditionsOperation in experiment
98% at 79 - 100℃; for 1 h; General procedure: N,N-Dimethylformamide (0.5 mg, 0.0673 mmol) was added dropwise to a slurry of 2,3-dihydroxyquinoxaline (2.0 g,12.3 mmol) and thionyl chloride (2.92 g, 24.6 mmol) in1-chlorobutane (20 mL). The mixture was refluxed for 1h.Then cooled to ambient temperature, the obtained needles were filtered, washed with ethyl ether, and dried.2,3-Dichloroquinoxaline (2a): white needles, yield 98percent; mp100–102 °C(lit. 16 m.p. 100–102 °C); FT-IR (KBr, cm-1):3049, 1618, 1562,753; 1H NMR (350 MHz, CDCl3): δ 8.07–8.02 (m, 2H, ArH), 7.85–7.80 (m, 2H, ArH); 13C NMR(CDCl3): 143.3, 140.9, 131.6, 127.8. Anal. Calcd. forC8H4Cl2N2: C, 48.28; H, 2.03; N, 14.07. Found: C, 47.52; H,1.89; N, 14.15.
96% With thionyl chloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane for 2 h; Reflux 31 mlof 1,2-dichloroethane in 3.5ml (48.1 mmol) of thionyl chloride and 3.0g (18.5mmol) of 2,3-dihydroxy quinoxaline in the slurry after the saline is slowlycatalytic amounts of dimethylformamide do. The reaction mixture was refluxedfor 2 hours. After the reaction was complete and then concentrated completelydissolved into the 35 ml of 1,2- dichloroethane it gives back again tocompletely concentrated. When the solid product thus obtained wasrecrystallized using acetonitrile and distilled water to obtain a solid whiteneedle-like crystals of 3.5 g (96percent yield).
95% With thionyl chloride In 1,2-dichloro-ethane; N,N-dimethyl-formamide for 2 h; Reflux DMF (0.045 g, 0.00062 mol) was added dropwise to a slurry of 2,3-dihydroxyquinoxaline (2, 2.0 g,0.012 mol) and thionyl chloride (3.7 g, 0.031 mol) in 1,2-dichloroethane (20 mL). The resulting reactionmixture was heated to reflux for 2 h then concentrated to dryness. The residue was dissolved in1,2-dichloroethane (25 mL) and concentrated to dryness. The resulting solid was crystallized fromCH3CN/H2O, giving 2.3 g (95percent) of 3 as fine, off-white needles. m.p. 148–150 °C [55].
98% With thionyl chloride In N,N-dimethyl-formamide Comparative Example 2
Synthesis of 2,3-Dichloroquinoxaline
2,3-Dihydroxyquinoxaline (100.0 grams, 616.7 mmoles), thionyl chloride (350 mL) and dry DMF (5 mL) were added to a 500 mL flask.
The flask was connected to a condenser, which was connected to a dry column.
The mixture was gradually heated at reflux until the solid had completely dissolved, which took around 6 h.
Then excess thionyl chloride was removed under reduced pressure to yield 120.8 g (98percent) of crude 2,3-dichloroquinoxaline.
Recrystallizations from toluene gave 86.5 g (72percent) of white needles: mp 151-152° C.

Reference: [1] Revue Roumaine de Chimie, 2017, vol. 62, # 12, p. 903 - 906
[2] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 1, p. 149 - 153
[3] Molecules, 2012, vol. 17, # 4, p. 4533 - 4544
[4] Organometallics, 2014, vol. 33, # 7, p. 1617 - 1622
[5] Patent: KR2015/123096, 2015, A, . Location in patent: Paragraph 0111-0112; 0116-0118
[6] Journal of Heterocyclic Chemistry, 2009, vol. 46, # 2, p. 317 - 319
[7] Molecules, 2018, vol. 23, # 1,
[8] Journal of Medicinal Chemistry, 2014, vol. 57, # 19, p. 7955 - 7970
[9] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[10] Synthetic Communications, 2005, vol. 35, # 15, p. 1983 - 1987
[11] Pesticide Science, 1995, vol. 43, # 4, p. 263 - 266
[12] Patent: US4291033, 1981, A,
[13] Patent: US2010/48857, 2010, A1,
[14] Monatshefte fur Chemie, 2010, vol. 141, # 10, p. 1145 - 1151
[15] Organic and Biomolecular Chemistry, 2012, vol. 10, # 36, p. 7392 - 7401
[16] Medicinal Chemistry Research, 2013, vol. 22, # 4, p. 1660 - 1673
[17] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5303 - 5310
[18] Journal of Molecular Structure, 2017, vol. 1139, p. 238 - 246
[19] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 7, p. 1809 - 1814
  • 5
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  • [ 10026-13-8 ]
  • [ 2213-63-0 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 784
[2] Chemische Berichte, 1908, vol. 41, p. 800
  • 6
  • [ 15804-19-0 ]
  • [ 32998-25-7 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[2] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[3] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[4] Medicinal Chemistry Research, 2013, vol. 22, # 4, p. 1660 - 1673
  • 7
  • [ 15804-19-0 ]
  • [ 32998-25-7 ]
Reference: [1] Journal of the Chemical Society, 1955, p. 1804,1806
  • 8
  • [ 15804-19-0 ]
  • [ 6639-79-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 22, p. 4367 - 4379
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