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[ CAS No. 697300-73-5 ] {[proInfo.proName]}

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Chemical Structure| 697300-73-5
Chemical Structure| 697300-73-5
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Product Details of [ 697300-73-5 ]

CAS No. :697300-73-5 MDL No. :MFCD08272065
Formula : C5H4BrIN2 Boiling Point : -
Linear Structure Formula :- InChI Key :OYZOHRSCEASBER-UHFFFAOYSA-N
M.W : 298.91 Pubchem ID :17609441
Synonyms :

Calculated chemistry of [ 697300-73-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.06
TPSA : 38.91 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) : -6.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.79
Log Po/w (XLOGP3) : 1.85
Log Po/w (WLOGP) : 2.04
Log Po/w (MLOGP) : 1.92
Log Po/w (SILICOS-IT) : 2.35
Consensus Log Po/w : 1.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.35
Solubility : 0.133 mg/ml ; 0.000445 mol/l
Class : Soluble
Log S (Ali) : -2.29
Solubility : 1.54 mg/ml ; 0.00515 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.104 mg/ml ; 0.000348 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.22

Safety of [ 697300-73-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 697300-73-5 ]

* 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 [ 697300-73-5 ]
  • Downstream synthetic route of [ 697300-73-5 ]

[ 697300-73-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 697300-73-5 ]
  • [ 13534-99-1 ]
YieldReaction ConditionsOperation in experiment
97% With palladium on silica; hydrogen In ethanol at 20 - 30℃; 30 g of 3-bromo-5-iodopyridin-2-amine and 300 ml of ethanol were added1 g palladium / silica,First replace the air with nitrogen three times,And then replaced with hydrogen three times.Adjust the pressure of 0.05Mpa ~ 0.1Mpa,Temperature control at 20 ~ 30 , until the raw material reaction is complete.Filtration recovery catalyst,Concentrated part of the solvent,Add 300 ml of water,Then add 4.2 g of sodium hydroxide to neutralize,Cooled to 0 ~ 5 , filtered and dried.To give 16.8 g of 3-bromopyridin-2-amine,Yield 97percent.
Reference: [1] Patent: CN106432068, 2017, A, . Location in patent: Paragraph 0037; 0039; 0040; 0041
  • 2
  • [ 20511-12-0 ]
  • [ 697300-73-5 ]
YieldReaction ConditionsOperation in experiment
47% With N-Bromosuccinimide In acetonitrile at 20℃; for 72 h; Step 13-Bromo-5-iodopyridin-2-amine Procedure:To a stirred solution of 5-iodopyridin-2-amine (25.0 g, 113 mmol) in acetonitrile (500 mL) was added NBS (20.2 g, 113 mmol) slowly at room temperature. After the addition, the reaction mixture was stirred at room temperature for a further 72 h. The solvent was evaporated at 40° C. at reduced pressure and the residue was purified by column chromatography (silica gel, 200-300 mesh, ethyl acetate/petroleum ether 3:1, v/v) to give 3-bromo-5-iodopyridin-2-amine (15.9 g, 47percent) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 8.07 (s, 1H), 7.98-7.97 (m, 1H), 6.43 (brs, 1H). LC/MS: 298.9 [M+H]+.
47% With N-Bromosuccinimide In acetonitrile at 20℃; for 72 h; To a stirred solution of 5-iodopyridin-2-amine (25.0 g, 113 mmol) in acetonitrile (500 m was added NBS (20.2 g, 113 mmol) slowly at room temperature. After the addition, the reaction mixture was stirred at room temperature for a further 72 h. The solvent was evaporated at 40°C at reduced pressure and the residue was purified by column chromatography (silica gel, 200 - 300 mesh, ethyl acetate / petroleum ether 3: 1, v/v) to give 3-bromo-5-iodopyridin-2-amine (15.9 g, 47 percent) as a yellow solid. 1H NMR (300MHz, DMSO): δ 8.07 (s, 1H), 7.98 - 7.97 (m, 1H), 6.43 (brs, 1H). LC/MS: 298.9 [M+H]+.
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 10, p. 2453 - 2465
[2] Patent: US2012/309746, 2012, A1, . Location in patent: Page/Page column 32
[3] Patent: WO2012/163724, 2012, A1, . Location in patent: Page/Page column 51-52
  • 3
  • [ 13534-99-1 ]
  • [ 697300-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 24, p. 11022 - 11030
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