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[ CAS No. 916325-85-4 ] {[proInfo.proName]}

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Chemical Structure| 916325-85-4
Chemical Structure| 916325-85-4
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Product Details of [ 916325-85-4 ]

CAS No. :916325-85-4 MDL No. :MFCD11040726
Formula : C7H4BrN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JSXAWNXOASHZLY-UHFFFAOYSA-N
M.W : 242.03 Pubchem ID :45480265
Synonyms :

Calculated chemistry of [ 916325-85-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.55
TPSA : 78.87 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) : -6.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.67
Log Po/w (XLOGP3) : 1.37
Log Po/w (WLOGP) : 1.42
Log Po/w (MLOGP) : 0.99
Log Po/w (SILICOS-IT) : 1.57
Consensus Log Po/w : 1.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.65
Solubility : 0.542 mg/ml ; 0.00224 mol/l
Class : Soluble
Log S (Ali) : -2.63
Solubility : 0.569 mg/ml ; 0.00235 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.77
Solubility : 0.41 mg/ml ; 0.00169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 916325-85-4 ]

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 [ 916325-85-4 ]

* 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 [ 916325-85-4 ]
  • Downstream synthetic route of [ 916325-85-4 ]

[ 916325-85-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 916325-84-3 ]
  • [ 916325-85-4 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium hydroxide; water In methanol for 4 h; Heating / reflux
Stage #2: With hydrogenchloride In methanol; water at 20℃;
Compound Ib (3.4 g, 13.2 mmol) in MeOH (50 mL) was refluxed with 2MNaOH (10 mL) for 4 hrs. The mixture was cooled to room temperature and acidified with hydrochloric acid to give Compound Ic (3.22 g, 100percent). 1H NMR (300 MHz,CD3OD) δ 8.62 (s, IH), 8.58 (s, IH);' MS (ESI) m/z: 359 (M+H+).
92%
Stage #1: at 90℃; for 3 h;
Stage #2: With hydrogenchloride In water at 0℃;
Step 7[00181] A suspension of methyl 5-bromo-lH-pyrazolo[3,4-.pound.]pyridine-3- carboxylate (VII) (70 mg, 0.27 mmol) in aqueous IN NaOH solution (20 mL) was heated at 90°C for 3 h until the solution became clear. The solution was then cooled to 0°C and acidified with a 10percent> HC1 solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-lH-pyrazolo[3,4- .pound.]pyridine-3-carboxylic acid (VIII) as a white solid (60 mg, 0.25 mmol, 92percent yield). 1H NMR (CDCls) δ ppm 8.58 (d, J=3.01 Hz, 1 H), 8.66 (d, J=3.01 Hz, 1 H); ESIMS found for C7H4BrN302 mlz 242.1 (M+H).
92%
Stage #1: With sodium hydroxide In water at 90℃; for 3 h;
Stage #2: With hydrogenchloride In water at 0℃;
spension of methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XVII) (70 mg, 0.27 mmol) in aqueous 1N NaOH solution (20 mL) was heated at 90° C. for 3 h until the solution became clear. The solution was then cooled to 0° C. and acidified with a 10percent HCl solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XVIII) as a white solid (60 mg, 0.25 mmol, 92percent yield). 1H NMR (CDCl3) δ ppm 8.58 (d, J=3.01 Hz, 1H), 8.66 (d, J=3.01 Hz, 1H); ESIMS found for C7H4BrN3O2 m/z 242.1 (M+H).
92% at 90℃; for 3 h; Step 7
A suspension of methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XV) (70 mg, 0.27 mmol) in aqueous 1N NaOH solution (20 mL) was heated at 90° C. for 3 h until the solution became clear.
The solution was then cooled to 0° C. and acidified with a 10percent HCl solution.
The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XVI) as a white solid (60 mg, 0.25 mmol, 92percent yield).
1H NMR (CDCl3) δ ppm 8.58 (d, J=3.01 Hz, 1H), 8.66 (d, J=3.01 Hz, 1H); ESIMS found for C7H4BrN3O2 m/z 242.1 (M+H).
92% at 0 - 90℃; for 3 h; A suspension of methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XV) (70 mg, 0.27 mmol) in aqueous IN NaOH solution (20 mL) was heated at 90°C for 3 h until the solution became clear. The solution was then cooled to 0°C and acidified with a 10percent HC1 solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XVI) as a white solid (60 mg, 0.25 mmol, 92percent yield). 1H NMR (CDCl3) δ ppm 8.58 (d, J=3.01Hz, 1H), 8.66 (d, J=3.01Hz, 1H); ESIMS found for C7H4BrN3O2 m/z 242.1 (M+H).

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4297 - 4302
[2] Patent: WO2006/130673, 2006, A1, . Location in patent: Page/Page column 74
[3] Patent: WO2011/84486, 2011, A1, . Location in patent: Page/Page column 106; 112-113
[4] Patent: US2013/296302, 2013, A1, . Location in patent: Paragraph 0499
[5] Patent: US2016/68550, 2016, A1, . Location in patent: Paragraph 1061
[6] Patent: WO2016/40193, 2016, A1, . Location in patent: Paragraph 0708
  • 2
  • [ 116834-96-9 ]
  • [ 916325-85-4 ]
Reference: [1] Inorganic Chemistry, 2011, vol. 50, # 22, p. 11715 - 11728
[2] Patent: WO2011/84486, 2011, A1,
[3] Patent: US2013/296302, 2013, A1,
[4] Patent: US2013/296302, 2013, A1,
[5] Patent: US2016/68550, 2016, A1,
[6] Patent: WO2016/40193, 2016, A1,
  • 3
  • [ 916325-83-2 ]
  • [ 916325-85-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4297 - 4302
[2] Patent: WO2011/84486, 2011, A1,
[3] Patent: US2013/296302, 2013, A1,
[4] Patent: US2016/68550, 2016, A1,
[5] Patent: WO2016/40193, 2016, A1,
[6] Patent: WO2006/130673, 2006, A1,
  • 4
  • [ 55676-21-6 ]
  • [ 916325-85-4 ]
Reference: [1] Patent: WO2011/84486, 2011, A1,
[2] Patent: US2013/296302, 2013, A1,
[3] Patent: US2013/296302, 2013, A1,
[4] Patent: US2016/68550, 2016, A1,
[5] Patent: WO2016/40193, 2016, A1,
  • 5
  • [ 109-09-1 ]
  • [ 916325-85-4 ]
Reference: [1] Patent: WO2011/84486, 2011, A1,
[2] Patent: US2013/296302, 2013, A1,
[3] Patent: US2013/296302, 2013, A1,
[4] Patent: US2016/68550, 2016, A1,
[5] Patent: WO2016/40193, 2016, A1,
  • 6
  • [ 131674-39-0 ]
  • [ 916325-85-4 ]
Reference: [1] Patent: WO2011/84486, 2011, A1,
[2] Patent: US2013/296302, 2013, A1,
[3] Patent: US2013/296302, 2013, A1,
[4] Patent: US2016/68550, 2016, A1,
[5] Patent: WO2016/40193, 2016, A1,
  • 7
  • [ 116855-08-4 ]
  • [ 916325-85-4 ]
Reference: [1] Patent: WO2011/84486, 2011, A1,
[2] Patent: US2013/296302, 2013, A1,
[3] Patent: US2016/68550, 2016, A1,
[4] Patent: WO2016/40193, 2016, A1,
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