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[ CAS No. 499-81-0 ] {[proInfo.proName]}

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Chemical Structure| 499-81-0
Chemical Structure| 499-81-0
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Product Details of [ 499-81-0 ]

CAS No. :499-81-0 MDL No. :MFCD00006393
Formula : C7H5NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :MPFLRYZEEAQMLQ-UHFFFAOYSA-N
M.W : 167.12 Pubchem ID :10366
Synonyms :

Calculated chemistry of [ 499-81-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 38.16
TPSA : 87.49 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) : -7.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.21
Log Po/w (XLOGP3) : -0.1
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : -1.47
Log Po/w (SILICOS-IT) : 0.12
Consensus Log Po/w : -0.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.05
Solubility : 14.9 mg/ml ; 0.0889 mol/l
Class : Very soluble
Log S (Ali) : -1.28
Solubility : 8.68 mg/ml ; 0.0519 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.77
Solubility : 28.7 mg/ml ; 0.172 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.22

Safety of [ 499-81-0 ]

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 [ 499-81-0 ]

* 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 [ 499-81-0 ]
  • Downstream synthetic route of [ 499-81-0 ]

[ 499-81-0 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 591-22-0 ]
  • [ 3222-49-9 ]
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Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
  • 2
  • [ 499-81-0 ]
  • [ 20730-07-8 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
  • 3
  • [ 499-81-0 ]
  • [ 36052-25-2 ]
Reference: [1] Patent: WO2009/42694, 2009, A1, . Location in patent: Page/Page column 95
  • 4
  • [ 591-22-0 ]
  • [ 499-81-0 ]
Reference: [1] Journal of Molecular Structure, 2007, vol. 837, # 1-3, p. 185 - 189
[2] Chemische Berichte, 1904, vol. 37, p. 2063[3] Chem. Zentralbl., 1903, vol. 74, # I, p. 1034
[4] Chemische Berichte, 1890, vol. 23, p. 1111
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1989, p. 851 - 858
  • 5
  • [ 4591-55-3 ]
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  • [ 5027-65-6 ]
Reference: [1] Patent: WO2016/67043, 2016, A1, . Location in patent: Page/Page column 150
  • 6
  • [ 59-67-6 ]
  • [ 74-88-4 ]
  • [ 499-81-0 ]
Reference: [1] Patent: US5125956, 1992, A,
  • 7
  • [ 591-22-0 ]
  • [ 3222-49-9 ]
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Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
  • 8
  • [ 110-86-1 ]
  • [ 124-38-9 ]
  • [ 59-67-6 ]
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  • [ 100-26-5 ]
  • [ 490-11-9 ]
Reference: [1] Chemical Physics, 2016, vol. 472, p. 173 - 184
  • 9
  • [ 871890-30-1 ]
  • [ 499-81-0 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1925, vol. 57, p. 332,334[2] Chem. Zentralbl., 1926, vol. 97, # I, p. 3337
  • 10
  • [ 110-86-1 ]
  • [ 124-38-9 ]
  • [ 59-67-6 ]
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  • [ 100-26-5 ]
  • [ 490-11-9 ]
Reference: [1] Chemical Physics, 2016, vol. 472, p. 173 - 184
  • 11
  • [ 67-56-1 ]
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  • [ 4591-55-3 ]
YieldReaction ConditionsOperation in experiment
94% for 18 h; Reflux 2,6-Pyridine dicarboxylic acid (5.00 g, 29.92 mmol) was dissolved in MeOH (100 ml) and concentrated sulfuric acid (2 ml) was slowly added thereto and refluxed for 18 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the mixture was extracted with sodium bicarbonate and dichloromethane. The dichloromethane layer was washed with a saturated sodium chloride aqueous solution to obtain 5.5 g (94percent) of compound l1
82% at 50 - 65℃; 4)
To a mixture of pyridine-3,5-dicarboxylic acid (110 g, 0.66 mol) and methanol (660 mL) was added dropwise conc. sulfuric acid (226.0 g, 2.30 mol) at 50° C. or lower.
Thereafter, the mixture was heated to 55-65° C. and stirred for 7 hr.
The reaction mixture was allowed to cool to 40-50° C., and water (220 mL) was added.
Furthermore, 5percent aqueous ammonia (about 1.10 L) was added dropwise at 40-50° C. to adjust the mixture to pH 8.0-8.5.
After stirring at 40-50° C. for 30 min, the mixture was cooled to 0-10° C. and stirred for 1 hr.
The precipitated crystals were collected by filtration, washed successively with methanol-water (1:3, 165 mL) and water (440 mL), and dried under reduced pressure at 50° C. to give dimethyl pyridine-3,5-dicarbonate as a white crystalline powder (105.0 g, yield 82.0percent).
1H-NMR (300 MHz, CDCl3) δ 4.00 (s, 6H), 8.87 (s, 1H), 9.37 (s, 2H).
Anal. Calcd for C9H9NO4: C, 55.39; H, 4.65; N, 7.18; O, 32.79. Found: C, 55.42; H, 4.65; N, 7.16.
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 10, p. 933 - 938
[2] Patent: KR2018/9249, 2018, A, . Location in patent: Paragraph 0250; 0251
[3] Angewandte Chemie - International Edition, 2004, vol. 43, # 30, p. 3914 - 3918
[4] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 9, p. 2397 - 2400
[5] Life Sciences, 2005, vol. 78, # 5, p. 495 - 505
[6] Chemical Communications, 2011, vol. 47, # 15, p. 4547 - 4549
[7] Patent: US2013/90337, 2013, A1, . Location in patent: Paragraph 0086; 0087; 0088
[8] Organic Letters, 2004, vol. 6, # 6, p. 1033 - 1036
[9] European Journal of Organic Chemistry, 2003, # 22, p. 4406 - 4412
[10] Angewandte Chemie - International Edition, 2014, vol. 53, # 43, p. 11660 - 11664[11] Angew. Chem., 2014, vol. 126, # 43, p. 11846 - 11850,5
[12] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 1, p. 101 - 103
[13] Phytochemistry (Elsevier), 1984, vol. 23, # 6, p. 1225 - 1228
[14] Patent: US2008/319018, 2008, A1, . Location in patent: Page/Page column 17
[15] Patent: US2009/233920, 2009, A1, . Location in patent: Page/Page column 83; 86
[16] Patent: US2010/137587, 2010, A1, . Location in patent: Page/Page column 48
[17] Patent: EP2202228, 2010, A1, . Location in patent: Page/Page column 90
[18] Photochemistry and Photobiology, 2013, vol. 89, # 5, p. 1020 - 1028
[19] Dalton Transactions, 2013, vol. 42, # 46, p. 16255 - 16258
[20] Patent: WO2015/58163, 2015, A2, . Location in patent: Paragraph 355
[21] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 415 - 422
[22] Patent: WO2006/117183, 2006, A1, . Location in patent: Page/Page column 134-135
  • 12
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YieldReaction ConditionsOperation in experiment
78% With thionyl chloride; sodium chloride; sodium hydrogencarbonate In methanol [Step 1]
Synthesis of dimethyl pyridine-3,5-dicarboxylate
Pyridine-3,5-dicarboxylic acid (8.3 g) was suspended in anhydrous methanol (60 ml), and thionyl chloride (11 ml) was added dropwise at room temperature.
The mixture was heated under reflux for 1.5 hours in an argon atmosphere and allowed to cool.
The solvent was evaporated under reduced pressure, and extracted with water-ethyl acetate.
The ethyl acetate layer was washed with saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate.
The solvent was evaporated under reduced pressure to obtain the title compound (7.5 g, 78percent).
m.p.: 83.5-84.5° C.
IR spectrum (KBr tab.) νcm-1: 1734, 1603, 1315, 1269, 1240, 995, 746.
NMR spectrum (*DMSO-d6) δ ppm: 9.30 (2H, s), 8.66 (1H, s), 3.93 (6H, s).
Reference: [1] Patent: US6018046, 2000, A,
[2] Journal of Materials Chemistry, 2002, vol. 12, # 2, p. 173 - 180
[3] Patent: WO2008/10964, 2008, A1,
  • 13
  • [ 499-81-0 ]
  • [ 64-17-5 ]
  • [ 4591-56-4 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 647 - 653
[2] Organic Letters, 2004, vol. 6, # 6, p. 1033 - 1036
[3] Chemical Science, 2015, vol. 6, # 2, p. 1444 - 1453
[4] Organometallics, 2013, vol. 32, # 1, p. 95 - 103
[5] Advanced Synthesis and Catalysis, 2009, vol. 351, # 18, p. 3045 - 3050
[6] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
[7] Pharmaceutical Bulletin, 1953, vol. 1, p. 142,145[8] Chem.Abstr., 1956, p. 11367
[9] Organic and Biomolecular Chemistry, 2015, vol. 13, # 1, p. 185 - 198
  • 14
  • [ 499-81-0 ]
  • [ 4591-56-4 ]
Reference: [1] Chemische Berichte, 1955, vol. 88, p. 789,794
[2] Patent: US4540564, 1985, A,
[3] Patent: US4824850, 1989, A,
  • 15
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  • [ 64-17-5 ]
  • [ 84254-37-5 ]
  • [ 4591-56-4 ]
Reference: [1] Patent: US2006/235028, 2006, A1, . Location in patent: Page/Page column 30
  • 16
  • [ 499-81-0 ]
  • [ 4663-99-4 ]
Reference: [1] Synthesis (Germany), 2014, vol. 46, # 9, p. 1243 - 1253
[2] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 1, p. 221 - 226
[3] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
  • 17
  • [ 499-81-0 ]
  • [ 75-65-0 ]
  • [ 337904-92-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 23, p. 4201 - 4204
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