Home Cart 0 Sign in  
X

[ CAS No. 116834-96-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 116834-96-9
Chemical Structure| 116834-96-9
Chemical Structure| 116834-96-9
Structure of 116834-96-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 116834-96-9 ]

Related Doc. of [ 116834-96-9 ]

Alternatived Products of [ 116834-96-9 ]
Product Citations

Product Details of [ 116834-96-9 ]

CAS No. :116834-96-9 MDL No. :MFCD09607943
Formula : C7H7N3 Boiling Point : -
Linear Structure Formula :- InChI Key :STHBHEYNLYNJAM-UHFFFAOYSA-N
M.W : 133.15 Pubchem ID :10582825
Synonyms :

Calculated chemistry of [ 116834-96-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.85
TPSA : 41.57 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) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.85
Log Po/w (XLOGP3) : 1.22
Log Po/w (WLOGP) : 1.27
Log Po/w (MLOGP) : 0.92
Log Po/w (SILICOS-IT) : 2.03
Consensus Log Po/w : 1.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.06 mg/ml ; 0.00794 mol/l
Class : Soluble
Log S (Ali) : -1.69
Solubility : 2.72 mg/ml ; 0.0204 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.89
Solubility : 0.171 mg/ml ; 0.00129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 116834-96-9 ]

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 [ 116834-96-9 ]

* 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 [ 116834-96-9 ]
  • Downstream synthetic route of [ 116834-96-9 ]

[ 116834-96-9 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 55676-21-6 ]
  • [ 116834-96-9 ]
YieldReaction ConditionsOperation in experiment
85% With hydrazine In ethanol for 12 h; Heating / reflux Step 3:
3-Methyl-1H-pyrazolo[3,4b]pyridine
A solution of 1-(2-chloropyridin-3-yl)ethanone (22 g, 0.1415 mol) and hydrazine hydrate 98percent (113 g, 2.21 mol) in ethanol (300 mL) was refluxed for 12 h.
About 80percent of the ethanol was distilled off under reduced pressure using a rotary evaporator.
The residue was allowed to come to room temperature.
The precipitated solid was filtered and washed with water.
The product was dried at 90° C. to constant weight (16 g, 85percent) mp 152-154° C. 1H NMR (CDCl3) 8.62 (dd, J=4.5 and 1.4 Hz, 1H), 8.08 (dd, J=8.0 and 1.4 Hz, 1H), 7.15 (dd J=8.0 and 4.5 Hz, 1H), 2.64 (s, 3H). MS (FAB) m/z: 133 (M++1).
85% With hydrazine hydrate In ethanol for 12 h; Reflux Step 3: 3-Methyl-lH-pyrazolo[3,4b]pyridine. A solution of l-(2-chloropyridin-3-yl)ethanone (22 g, 0.1415 mol) and hydrazine hydrate 98percent (113 g, 2.21 mol) in ethanol (300 mL) was refluxed for 12 h. About 80percent of the ethanol was distilled off under reduced pressure using a rotary evaporator. The residue was allowed to come to room temperature. The precipitated solid was filtered and washed with water. The product was dried at 90 0C to constant weight (16 g, 85percent) mp 152-154 0C. 1H NMR (CDCl3) 8.62 (dd, J = 4.5 and 1.4 Hz, 1 H), 8.08 (dd, J = 8.0 and 1.4 Hz, 1 H), 7.15 (dd J = 8.0 and 4.5 Hz, 1 H), 2.64 (s, 3 H). MS (FAB) m/z: 133 (M+ +1).
72% With hydrazine hydrate In butan-1-olReflux Step 3[00177] To a solution of l-(2-Chloropyridin-3-yl)ethanone (III) (0.311 g, 2 mmol) in n-butanol (10 mL) was added hydrazine hydrate (1.45 mL, 30 mmol). The reaction was refluxed overnight. The solution was cooled and the solvent was evaporated under vacuum. The residue was dissolved in DCM and washed successively by water and brine. The organic layers were dried over MgS04, filtered and concentrated under reduced pressure to give 3-methyl-lH-pyrazolo[3,4-.pound.]pyridine (IV) as a white solid (192 mg, 1.44 mmol, 72percent yield). 1H NMR (CDC13) δ ppm 2.64 (s, 3 H), 7.14 (dd, J=8.01, 4.62 Hz, 1 H), 8.14 (dd, J=7.54, 1.88 HZ, 1 H), 8.59 (dd, J=4.52, 1.32 HZ, 1 H), 11.68 (brs, 1H).
72% With hydrazine hydrate In butan-1-olReflux To a solution of 1-(2-Chloropyridin-3-yl)ethanone (XIII) (0.311 g, 2 mmol) in n-butanol (10 mL) was added hydrazine hydrate (1.45 mL, 30 mmol). The reaction was refluxed overnight. The solution was cooled and the solvent was evaporated under vacuum. The residue was dissolved in DCM and washed successively by water and brine. The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to give 3-methyl-1H-pyrazolo[3,4-b]pyridine (XIV) as a white solid (192 mg, 1.44 mmol, 72percent yield). 1H NMR (CDCl3) δ ppm 2.64 (s, 3H), 7.14 (dd, J=8.01 Hz, J=4.62 Hz, 1H), 8.14 (dd, J=7.54 Hz, J=1.88 Hz, 1H), 8.59 (dd, J=4.52 Hz, J=1.32 Hz, 1H), 11.68 (brs, 1H)
72% With hydrazine hydrate In butan-1-olReflux Step 3
To a solution of 1-(2-chloropyridin-3-yl)ethanone (XI) (0.311 g, 2 mmol) in n-butanol (10 mL) was added hydrazine hydrate (1.45 mL, 30 mmol).
The reaction was refluxed overnight.
The solution was cooled and the solvent was evaporated under vacuum.
The residue was dissolved in DCM and washed successively by water and brine.
The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to give 3-methyl-1H-pyrazolo[3,4-b]pyridine (XII) as a white solid (192 mg, 1.44 mmol, 72percent yield).
1H NMR (CDCl3) δ ppm 2.64 (s, 3H), 7.14 (dd, J=8.01 Hz, J=4.62 Hz, 1H), 8.14 (dd, J=7.54 Hz, J=1.88 Hz, 1H), 8.59 (dd, J=4.52 Hz, J=1.32 Hz, 1H), 11.68 (brs, 1H).
72% With hydrazine hydrate In butan-1-olReflux To a solution of 1-(2-chloropyridin-3-yl)ethanone (XI) (0.31 1 g, 2 mmol) in n-butanol (10 mL) was added hydrazine hydrate (1.45 mL, 30 mmol). The reaction was refluxed overnight. The solution was cooled and the solvent was evaporated under vacuum. The residue was dissolved in DCM and washed successively by water and brine. The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to give 3-methyl-1H-pyrazolo [3,4-b]pyridine (XII) as a white solid (192 mg, 1.44 mmol, 72percent yield). 1H NMR (CDCl3) δ ppm 2.64 (s, 3 H), 7.14 (dd, J=8.01Hz, J=4.62Hz, 1H), 8.14 (dd, J=7.54Hz, J=1.88Hz, 1H), 8.59 (dd, J=4.52Hz, J=1.32Hz, 1H), 1 1.68 (brs, 1H).

Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 57, p. 311 - 322
[2] Patent: US2006/47126, 2006, A1, . Location in patent: Page/Page column 30
[3] Patent: WO2011/5759, 2011, A2, . Location in patent: Page/Page column 77-78
[4] Canadian Journal of Chemistry, 1988, vol. 66, # 3, p. 420-428
[5] Patent: WO2011/84486, 2011, A1, . Location in patent: Page/Page column 106; 111
[6] Patent: US2013/296302, 2013, A1, . Location in patent: Paragraph 0495
[7] Patent: US2016/68550, 2016, A1, . Location in patent: Paragraph 1057
[8] Patent: WO2016/40193, 2016, A1, . Location in patent: Paragraph 0704
[9] Patent: WO2005/9958, 2005, A1, . Location in patent: Page 180
[10] Patent: WO2011/79804, 2011, A1, . Location in patent: Page/Page column 24
[11] Patent: US2012/245178, 2012, A1, . Location in patent: Page/Page column 13
[12] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7577 - 7589
  • 2
  • [ 372-48-5 ]
  • [ 78191-00-1 ]
  • [ 116834-96-9 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere
Stage #2: With hydrazine hydrate In tetrahydrofuran; hexane at -78 - 60℃; for 1 h; Inert atmosphere
Example 2(1)3-Methyl-1H-pyrazolo[3,4-b]pyridine (2a)Normal-butyllithium (a 2.6 M solution in hexane, 87.0 mL) was dropwise added to a solution of N,N-diisopropylamine (11.2 mL) in THF (100 mL) at -78° C. under a nitrogen atmosphere, followed by increasing the temperature to 0° C. Then, the solution was cooled to -78° C., and a solution of 2-fluoropyridine (6.2 g) in THF (100 mL) was dropwise added thereto at -78° C., followed by stirring for 1 hr. Subsequently, a solution of N-methoxy-N-methylacetamide (8.46 mL) in THF (50 mL) was dropwise added to the reaction solution at -78° C., and then hydrazine monohydrate (31.9 mL) was added thereto, followed by stirring at 60° C. for 1 hr. After distillation of the solvent, water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and then the solvent was distilled away to obtain compound (2a) (5.90 g, 69percent) as a white solid.1H-NMR (DMSO-d6) δ 8.08 (1H, dd, J=4.27, 1.71 Hz), 7.79 (1H, dd, J=7.81, 1.71 Hz), 6.60 (1H, dd, J=7.81, 4.27 Hz), 2.44 (3H, s); LRMS (ESI) m/z 134 [M+H]+.
Reference: [1] Patent: US2012/108589, 2012, A1, . Location in patent: Page/Page column 14
  • 3
  • [ 79574-70-2 ]
  • [ 116834-96-9 ]
Reference: [1] Patent: US2007/21442, 2007, A1, . Location in patent: Page/Page column 53
[2] Medicinal Chemistry letters, 2012, vol. 3, # 8, p. 678 - 682,5
[3] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 8, p. 678 - 682
[4] Patent: WO2008/76223, 2008, A1, . Location in patent: Page/Page column 26
  • 4
  • [ 31230-17-8 ]
  • [ 116834-96-9 ]
Reference: [1] Patent: US5859007, 1999, A,
  • 5
  • [ 109-09-1 ]
  • [ 116834-96-9 ]
Reference: [1] Patent: WO2011/5759, 2011, A2,
[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
  • [ 131674-39-0 ]
  • [ 116834-96-9 ]
Reference: [1] Patent: WO2011/5759, 2011, A2,
[2] Patent: WO2011/84486, 2011, A1,
[3] Patent: US2013/296302, 2013, A1,
[4] Patent: US2016/68550, 2016, A1,
[5] Patent: WO2016/40193, 2016, A1,
  • 7
  • [ 2942-59-8 ]
  • [ 116834-96-9 ]
Reference: [1] Patent: WO2011/79804, 2011, A1,
[2] Patent: US2012/245178, 2012, A1,
[3] European Journal of Medicinal Chemistry, 2012, vol. 57, p. 311 - 322
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7577 - 7589
  • 8
  • [ 102-52-3 ]
  • [ 31230-17-8 ]
  • [ 116834-96-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 17, p. 2706 - 2725
  • 9
  • [ 350-03-8 ]
  • [ 116834-96-9 ]
Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, # 3, p. 420-428
  • 10
  • [ 14188-94-4 ]
  • [ 116834-96-9 ]
Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, # 3, p. 420-428
  • 11
  • [ 488149-34-4 ]
  • [ 116834-96-9 ]
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 57, p. 311 - 322
  • 12
  • [ 372-48-5 ]
  • [ 116834-96-9 ]
Reference: [1] Patent: WO2008/76223, 2008, A1,
  • 13
  • [ 116834-96-9 ]
  • [ 116855-08-4 ]
YieldReaction ConditionsOperation in experiment
81% at 80 - 90℃; Step 4[00178] To a solution of NaOH (0.88 g, 22 mmol) in water (20 mL) was added 3-methyl-lH-pyrazolo[3,4-.pound.]pyridine (IV) (0.4 g, 3 mmol). The suspension was heated at 80°C until a clear solution was obtained. A solution of KMn04 (1.73 g, 11 mmol) in water (180 mL) was added slowly over 2 h while heating the solution at 80°C. The solution was heated at 90°C for an additional 2 h until the complete disappearance of starting material was observed by TLC. The solution was cooled to 70°C and filtered through a pad of Celite. The solids were washed by boiling water. The combined filtrate was cooled to 0°C, acidified with cone. H2S04 to pH=2 and extracted with n-butanol (2 x 10 mL). The n-butanol layer was concentrated under reduced pressure to get a white residue which was dissolved in DCM by adding minimum amount of MeOH and then filtered. The filtrate was concentrated to give lH-pyrazolo[3,4-3/4]pyridine-3-carboxylic acid (V) as a white solid (390 mg, 2.39 mmol, 81percent yield). 1H NMR (CDC13) δ ppm 7.37 (dd, J=8.10, 4.52 Hz, 1 H), 8.47 (dd, J=7.54, 1.88 Hz, 1 H), 8.62 (dd, J=4.52, 1.32 Hz, 1 H), 14.37 (brs, 1 H).
81%
Stage #1: With sodium hydroxide In water at 80℃;
Stage #2: With potassium permanganate In water at 80 - 90℃; for 4 h;
To a solution of NaOH (0.88 g, 22 mmol) in water (20 mL) was added 3-methyl-1H-pyrazolo[3,4-b]pyridine (XIV) (0.4 g, 3 mmol). The suspension was heated at 80° C. until a clear solution was obtained. A solution of KMnO4 (1.73 g, 11 mmol) in water (180 mL) was added slowly over 2 h while heating the solution at 80° C. The solution was heated at 90° C. for an additional 2 h until the complete disappearance of starting material was observed by TLC. The solution was cooled to 70° C. and filtered through a pad of Celite. The solids were washed by boiling water. The combined filtrate was cooled to 0° C., acidified with cone. H2SO4 to pH=2 and extracted with n-butanol (2×10 mL). The n-butanol layer was concentrated under reduced pressure to get a white residue which was dissolved in DCM by adding minimum amount of MeOH and then filtered. The filtrate was concentrated to give 1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XV) as a White solid (390 mg, 2.39 mmol, 81percent yield). 1H NMR (CDCl3) δ ppm 7.37 (dd, J=8.10 Hz, J=4.52 Hz, 1H), 8.47 (dd, J=7.54 Hz, J=1.88 Hz, 1H), 8.62 (dd, J=4.52 Hz, J=1.32 Hz, 1H), 14.37 (brs, 1H).
81% With potassium permanganate; sodium hydroxide In water at 80 - 90℃; for 4 h; Step 4
To a solution of NaOH (0.88 g, 22 mmol) in water (20 mL) was added 3-methyl-1H-pyrazolo[3,4-b]pyridine (XII) (0.4 g, 3 mmol).
The suspension was heated at 80° C. until a clear solution was obtained.
A solution of KMnO4 (1.73 g, 11 mmol) in water (180 mL) was added slowly over 2 h while heating the solution at 80° C.
The solution was heated at 90° C. for an additional 2 h until the complete disappearance of starting material was observed by TLC.
The solution was cooled to 70° C. and filtered through a pad of Celite.
The solids were washed by boiling water.
The combined filtrate was cooled to 0° C., acidified with conc. H2SO4 to pH=2 and extracted with n-butanol (2*10 mL).
The n-butanol layer was concentrated under reduced pressure to get a white residue which was dissolved in DCM by adding minimum amount of MeOH and then filtered.
The filtrate was concentrated to give 1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XIII) as a white solid (390 mg, 2.39 mmol, 81percent yield).
1H NMR (CDCl3) δ ppm 7.37 (dd, J=8.10 Hz, J=4.52 Hz, 1H), 8.47 (dd, J=7.54 Hz, J=1.88 Hz, 1H), 8.62 (dd, J=4.52 Hz, J=1.32 Hz, 1H), 14.37 (brs, 1H).
81% With potassium permanganate; sodium hydroxide In water at 70 - 90℃; for 4 h; To a solution of NaOH (0.88 g, 22 mmol) in water (20 mL) was added 3-methyl-1H-pyrazolo[3,4-b]pyridine (XII) (0.4 g, 3 mmol). The suspension was heated at 80°C until a clear solution was obtained. A solution of KMnC (1.73 g, 1 1 mmol) in water (180 mL) was added slowly over 2 h while heating the solution at 80°C. The solution was heated at 90°C for an additional 2 h until the complete disappearance of starting material was observed by TLC. The solution was cooled to 70°C and filtered through a pad of Celite. The solids were washed by boiling water. The combined filtrate was cooled to 0°C, acidified with cone. H2SO4 to pH=2 and extracted with n-butanol (2 x 10 mL). The n-butanol layer was concentrated under reduced pressure to get a white residue which was dissolved in DCM by adding minimum amount of MeOH and then filtered. The filtrate was concentrated to give 1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XIII) as a white solid (390 mg, 2.39 mmol, 81percent yield). 1H NMR (CDCl3) δ ppm 7.37 (dd, J=8.10Hz, J=4.52Hz, 1H), 8.47 (dd, J=7.54Hz, J=1.88Hz, 1H), 8.62 (dd, J=4.52Hz, J=1.32Hz, 1H), 14.37 (brs, 1H).

Reference: [1] Patent: WO2011/84486, 2011, A1, . Location in patent: Page/Page column 106; 111-112
[2] Patent: US2013/296302, 2013, A1, . Location in patent: Paragraph 0496
[3] Patent: US2016/68550, 2016, A1, . Location in patent: Paragraph 1058
[4] Patent: WO2016/40193, 2016, A1, . Location in patent: Paragraph 0705
[5] Canadian Journal of Chemistry, 1988, vol. 66, # 3, p. 420-428
[6] Patent: US2006/47126, 2006, A1, . Location in patent: Page/Page column 30-31
[7] Patent: WO2011/5759, 2011, A2, . Location in patent: Page/Page column 78
  • 14
  • [ 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,
  • 15
  • [ 116834-96-9 ]
  • [ 916325-83-2 ]
Reference: [1] Patent: WO2011/5759, 2011, A2,
[2] Patent: WO2011/84486, 2011, A1,
[3] Patent: US2013/296302, 2013, A1,
[4] Patent: US2016/68550, 2016, A1,
[5] Patent: WO2016/40193, 2016, A1,
Recommend Products
Same Skeleton Products
Historical Records

Related Parent Nucleus of
[ 116834-96-9 ]

Other Aromatic Heterocycles

Chemical Structure| 76006-17-2

[ 76006-17-2 ]

1H-Pyrazolo[3,4-c]pyridin-3-amine

Similarity: 0.77

Chemical Structure| 6752-16-5

[ 6752-16-5 ]

1H-Pyrazolo[3,4-b]pyridin-3-amine

Similarity: 0.66

Chemical Structure| 271-52-3

[ 271-52-3 ]

1H-Pyrazolo[4,3-c]pyridine

Similarity: 0.60

Chemical Structure| 271-47-6

[ 271-47-6 ]

1H-Pyrazolo[3,4-c]pyridine

Similarity: 0.59

Chemical Structure| 157327-44-1

[ 157327-44-1 ]

4,5,6,7-Tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride

Similarity: 0.59