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[ CAS No. 21427-62-3 ] {[proInfo.proName]}

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Chemical Structure| 21427-62-3
Chemical Structure| 21427-62-3
Structure of 21427-62-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 21427-62-3 ]

CAS No. :21427-62-3 MDL No. :MFCD06658963
Formula : C5H2Cl2N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OBUGJYJQJWMOQO-UHFFFAOYSA-N
M.W : 192.99 Pubchem ID :8063331
Synonyms :

Calculated chemistry of [ 21427-62-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.08
TPSA : 58.71 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) : -5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : 2.31
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 0.49
Log Po/w (SILICOS-IT) : 0.59
Consensus Log Po/w : 1.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.83
Solubility : 0.286 mg/ml ; 0.00148 mol/l
Class : Soluble
Log S (Ali) : -3.18
Solubility : 0.127 mg/ml ; 0.000659 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.64
Solubility : 0.441 mg/ml ; 0.00229 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.02

Safety of [ 21427-62-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 21427-62-3 ]

* 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 [ 21427-62-3 ]
  • Downstream synthetic route of [ 21427-62-3 ]

[ 21427-62-3 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 21427-62-3 ]
  • [ 78607-32-6 ]
Reference: [1] ACS Catalysis, 2015, vol. 5, # 3, p. 1526 - 1529
[2] Science, 2013, vol. 342, # 6162, p. 1073 - 1076
[3] Patent: US4935051, 1990, A,
[4] Patent: US4713109, 1987, A,
[5] Journal of the Chemical Society, 1952, p. 2042,2044
[6] Patent: US4831148, 1989, A,
[7] Green Chemistry, 2015, vol. 17, # 2, p. 898 - 902
  • 2
  • [ 5409-39-2 ]
  • [ 21427-62-3 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With hydrogenchloride In water at -10℃;
Stage #2: With sodium nitrite In water at 0℃; for 2 h;
Stage #3: With sodium hydroxide In water at -10 - 0℃;
5-Chloro-3-nitro-2-pyridinamine (5.0 g, 28.8 mmol) was dissolved in cone. HCI (50 mL) and cooled to -10 0C in an ice-salt bath. Sodium nitrite (4.97 g, 72 mmol) in water (10 mL) was added dropwise to the cooled solution over 1 h and stirred at 0 °C for 1 h longer. The reaction mixture was cooled to -10 0C in an ice-salt bath and neutralized with 2N sodium hydroxide to pH 9.0 keeping the temperature below 0 0C. EtOAc (150 mL) was added and the mixture was filtered. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to afford the title compound as 3.36 g (60percent yield) of a light brown solid; 1H NMR (cfe-DMSO) δ 8.62 (d, 1 H, 2.5 Hz), 8.26 (d, 1 H, 2.2 Hz).
58.5% With hydrogenchloride; sodium nitrite In water at -10 - 0℃; for 1.5 h; 5-chloro-3-nitropyridine-2-amine 10.0g of (57.6 mmol) was dissolved in concentrated hydrochloric acid 100 mL, and stirred at -10 ° C.. Here, sodium nitrite 9.94g of (144 mmol) Yuki dropwise over 30 minutes a liquid obtained by dissolving water 20 mL, after the addition, the mixture was stirred 1 hour at 0 ° C.. By adding 1N aqueous sodium hydroxide solution to the reaction solution and pH 9, and extracted with ethyl acetate. Insolubles were removed by filtration, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. Filtered and the filtrate was evaporated under reduced pressure to give the title compound 6.50g of (58.5percent yield) as a solid.
58.5%
Stage #1: With hydrogenchloride; sodium nitrite In water at -10℃; for 0.5 h;
Stage #2: With sodium hydroxide In water at 0℃; for 1 h;
5-chloro-3-nitropyridine-2-amine 10.0g of (57.6 mmol) was dissolved in concentrated hydrochloric acid 100 mL, and stirred at -10 ° C.. Here, sodium nitrite 9.94g of (144 mmol) add dropwise over 30 minutes a liquid obtained by dissolving water 20 mL, after the addition, the mixture was stirred 1 hour at 0 ° C.. By adding 1N aqueous sodium hydroxide solution to the reaction solution and pH 9, and extracted with ethyl acetate. Insolubles were removed by filtration, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. Filtered and the filtrate was evaporated under reduced pressure to give the title compound 6.50g of (58.5percent yield) as a solid.
58.5% With hydrogenchloride; sodium nitrite In water at -10 - 0℃; for 1.5 h; (Step 1)
2,5-Dichloro-3-nitropyridine
5-Chloro-3-nitropyridin-2-amine (10.0 g, 57.6 mmol) was dissolved in concentrated hydrochloric acid (100 mL), and the solution was stirred at -10°C. A solution of sodium nitrite (9.94 g, 144 mmol) dissolved in water (20 mL) was added dropwise thereto over 30 minutes.
After the completion of the addition, the mixture was stirred at 0°C for 1 hour.
The pH of the reaction solution was adjusted to 9 by the addition of a 1 N aqueous sodium hydroxide solution, followed by extraction with ethyl acetate.
Insoluble matter was removed by filtration, and the organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate.
After filtration, the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (6.50 g, yield: 58.5percent) as a solid.
1H-NMR (CDCl3) δ: 8.60 (1H, d, J = 2.9 Hz), 8.24 (1H, d, J = 2.6 Hz).

Reference: [1] Patent: WO2007/67875, 2007, A2, . Location in patent: Page/Page column 15
[2] Patent: JP2016/56134, 2016, A, . Location in patent: Paragraph 0165; 0166; 0167
[3] Patent: JP2016/56133, 2016, A, . Location in patent: Paragraph 0158; 0159
[4] Patent: EP3109239, 2016, A1, . Location in patent: Paragraph 0189
[5] Journal of the Chemical Society, 1952, p. 2042,2044
[6] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2625 - 2637
[7] Patent: US2007/167435, 2007, A1, . Location in patent: Page/Page column 29
  • 3
  • [ 21427-61-2 ]
  • [ 21427-62-3 ]
Reference: [1] Journal of the Chemical Society, 1952, p. 2042,2044
[2] Roczniki Chemii, 1968, vol. 42, p. 2079,2084[3] Chem.Abstr., 1969, vol. 70, p. 106327
[4] Yakugaku Zasshi, 1952, vol. 72, p. 431[5] Chem.Abstr., 1953, p. 6404
[6] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980, vol. 16, # 12, p. 1234 - 1238[7] Khimiya Geterotsiklicheskikh Soedinenii, 1980, vol. 16, # 12, p. 1632 - 1636
[8] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 1, p. 73 - 76
[9] Patent: WO2005/97805, 2005, A1, . Location in patent: Page/Page column 57-58
[10] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3983 - 3987
  • 4
  • [ 75-44-5 ]
  • [ 21427-61-2 ]
  • [ 21427-62-3 ]
Reference: [1] Patent: US5274100, 1993, A,
  • 5
  • [ 21427-61-2 ]
  • [ 21427-62-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2625 - 2637
  • 6
  • [ 4214-79-3 ]
  • [ 21427-62-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2625 - 2637
  • 7
  • [ 5409-39-2 ]
  • [ 21427-61-2 ]
  • [ 21427-62-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2625 - 2637
  • 8
  • [ 4214-79-3 ]
  • [ 21427-62-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3983 - 3987
  • 9
  • [ 21427-62-3 ]
  • [ 544-92-3 ]
  • [ 181123-11-5 ]
Reference: [1] Patent: WO2005/97805, 2005, A1, . Location in patent: Page/Page column 57-58
  • 10
  • [ 21427-62-3 ]
  • [ 136888-26-1 ]
Reference: [1] Patent: US2015/203450, 2015, A1,
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