63572-73-6|5-Nitro-1H-pyrazolo[3,4-b]pyridine| Ambeed

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Quality Control of [ 63572-73-6 ] Purity: 95% SDS Specification

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Product Details of [ 63572-73-6 ]

CAS No. :	63572-73-6
Formula :	C₆H₄N₄O₂
M.W :	164.12
SMILES Code :	O=[N+](C1=CN=C(NN=C2)C2=C1)[O-]
MDL No. :	MFCD11215386
InChI Key :	RXLQRSOJODHPES-UHFFFAOYSA-N
Pubchem ID :	12352776

Safety of [ 63572-73-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 63572-73-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	42.71
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	87.39 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.39
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.65
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.87
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.35
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.6
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.33

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.76
Solubility	2.88 mg/ml ; 0.0175 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.06
Solubility	1.43 mg/ml ; 0.00869 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.91
Solubility	2.01 mg/ml ; 0.0123 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.84 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.97

Application In Synthesis of [ 63572-73-6 ]

* 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.

Downstream synthetic route of [ 63572-73-6 ]

[ 63572-73-6 ] Synthesis Path-Downstream 1~35

1
[ 34461-00-2 ]
[ 1225387-53-0 ]
[ 63572-73-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	In acetic acid; at 90℃;	A suspension of lH-pyrazol-5-amine (0.804 g, 9.48 mmol) and sodium nitromalonaldehyde monohydrate (1.56 g, 9.96 mmol) in acetic acid (12 mL) was heated to 9O0C overnight. The reaction mixture was cooled to room temperature and poured into water (50 mL). The resulting solids were collected by filtration. The solids were washed with water (3 X 20 mL) and dried in vacuo to give 5-nitro-l H-pyrazolo [3 ,4-b]pyridine (1.40 g, 84%) as a solid.
84%	In acetic acid; at 90℃;	A suspension of lH-pyrazol-5 -amine (0.804 g, 9.48 mmol) and sodium nitromalonaldehyde monohydrate (1.56 g, 9.96 mmol) in acetic acid (12 mL) was heated to 90C overnight. The reaction mixture was cooled to room temperature and poured into water (50 mL). The resulting solids were collected by filtration. The solids were washed with water (3 X 20 mL) and dried in vacuo to give 5-nitro-lH-pyrazolo[3,4-b]pyridine (1.40 g, 84%) as a solid.

References: [1]Patent: WO2011/25968,2011,A1 .Location in patent: Page/Page column 49.
[2]Patent: WO2009/111279,2009,A1 .Location in patent: Page/Page column 96.
[3]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 1335 - 1339.
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1560 - 1564.
[4]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 342 - 347.

2
[ 34461-00-2 ]
[ 1225387-53-0 ]
[ 63572-73-6 ]
[ 116835-08-6 ]

References: [1]Canadian Journal of Chemistry,1988,vol. 66,p. 420-428.

4
[ 63572-73-6 ]
[ 942185-01-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; ethanol; for 15h;	10 % Palladium on carbon (40 mg) was added to a solution of <strong>[63572-73-6]5-nitro-1H-pyrazolo[3,4-b]pyridine</strong> (A) (308 mg, 1.876 mmol) in ethanol and tetrahydrofuran and the mixture was charged with H2 (gas). After stirring the reaction mixture for 15 h, the mixture was filtered using celite and purified by column chromatography. The desired product 1H-pyrazolo[3,4-b]pyridin-5-amine (B) (73 mg) was obtained as 89 % yield.
89%	With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; ethanol; for 15h;	10% Palladium on carbon (40 mg) was added to a solution of <strong>[63572-73-6]5-nitro-1H-pyrazolo[3,4-b]pyridine</strong> (A) (308 mg, 1.876 mmol) in ethanol and tetrahydrofuran and the mixture was charged with H2 (gas). After stirring the reaction mixture for 15 h, the mixture was filtered using celite and purified by column chromatography. The desired product 1H-pyrazolo[3,4-b]pyridin-5-amine (B) (73 mg) was obtained as 89% yield.
82%	With palladium on activated carbon; hydrogen; In methanol; at 20℃; under 760.051 Torr; for 16h;	To a solution of 5-nitro-1H-pyrazolo [4,3-b]pyridine (7.3 g,38.0 mmol) in MeOH (240 mL) was added 10% wt Pd/C (4.03,3.8 mmol). The reaction mixture was hydrogenated underhydrogen (1 atm) for 16 h. The Pd/C was removed by filtration, andthe filtrate was concentrated to give 1H-pyrazolo [4,3-b]pyridin-5-amine (5.1 g, 82% yield) as a light brown solid. Rf: 0.33 (DCM/MeOH,19/1, v/v). Mp: 178 C. 1H NMR (DMSO-d6, 400 MHz) d 13.12 (s, 1H),8.05 (d, J 2.4 Hz, 1H), 7.81 (s, 1H), 7.18 (d, J 2.3 Hz, 1H), 5.04 (s,2H). MS (ESI)m/z:134.8 [MH],156.7 [MNa], 301.0 [2MNa].

5-Nitro--1H-pyrazolo[3,4-b]pyridine (prepared according to the procedure in Can. J. Chem. 1988, 66(3), 420) (133 mg, 0.81 mmol) was mixed with SnCI2 (1.0g) in EtOH/CH3Ph (4 mL/2mL) and heated at 70 0C for 3 hrs. The reaction was cooled to rt and concentrated to dryness. The residue was participated between 1.0 N NaOH (10 mL) and ethyl acetate (50 mL). The organic layer was washed with brine once, dried (MgSO4) and filtered. The filtrate was concentrated and the resulting crude was purified by prep. TLC using 10:2 CH2CI2/Methanol(2 N NH3). The title compound (15.0 mg) was isolated as a yellow solid.

References: [1]Patent: WO2013/13816,2013,A1 .Location in patent: Page/Page column 73; 74.
[2]Patent: US2013/29995,2013,A1 .Location in patent: Paragraph 0374-0375.
[3]European Journal of Medicinal Chemistry,2017,vol. 131,p. 1 - 13.
[4]Patent: WO2007/70398,2007,A1 .Location in patent: Page/Page column 249.

5
[ 63572-73-6 ]
[ 1186608-83-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 16h;	Compound 1 (2 g, 12.2 mmol, 1.0 eq),Soluble in DMF (20mL),NBS (2.5 g, 14.0 mmol, 1.15 eq) was added in portions at 0 C.The reaction was carried out for 16 hours at room temperature.LCMS showed the reaction of the starting material,There is product generation. Concentrate and spin dry to a crude product.Purified by column (PE/EA=100:1-10:1),Yellow solid compound 2 (1.4 g, yield: 94%).
88%		4N NaOH (5.12 mL, 20.5 mmol) was added to a cold (00C) solution of5-nitro-lH-pyrazolo[3,4-b]pyridine (0.84 g, 5.12 mmol) in dioxane (30 mL), followed by bromine (1.05 mL, 20.5 mmol). The cold bath was removed, and the reaction mixture was left at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate (100 mL) and quenched with saturated aqueous Na3S3O3 (50 mL). The aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried, filtered and concentrated.The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate(9:1) to give 3 -bromo-5-nitro-l H-pyrazolo [3 ,4-b]pyridine (1.10 g, 88%) as a solid.
88%	With bromine; sodium hydroxide; In 1,4-dioxane; at 0 - 20℃;	4N NaOH (5.12 mL, 20.5 mmol) was added to a cold (O0C) solution of 5-nitro-lH-pyrazolo[3,4-b]pyridine (0.84 g, 5.12 mmol) in dioxane (30 mL), followed by bromine (1.05 mL, 20.5 mmol). The cold bath was removed, and the reaction mixture was left at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate (100 mL) and quenched with saturated Na2S2O3 (50 mL). The aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (9:1) to give 3-bromo-5-nitro-lH-pyrazolo[3,4-b]pyridine (1.10 g, 88%) as a solid.

References: [1]Patent: CN109206401,2019,A .Location in patent: Paragraph 0111; 0112; 0113; 0114; 0115.
[2]Patent: WO2011/25968,2011,A1 .Location in patent: Page/Page column 49.
[3]Patent: WO2009/111279,2009,A1 .Location in patent: Page/Page column 96.
[4]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 342 - 347.

6
[ 63572-73-6 ]
[ 1186608-85-4 ]

References: [1]Patent: WO2011/25968,2011,A1 .
[2]Patent: WO2009/111279,2009,A1 .

7
[ 63572-73-6 ]
[ 1268718-34-8 ]

References: [1]Patent: WO2011/25968,2011,A1 .

8
[ 63572-73-6 ]
[ 124-40-3 ]
[ 1186608-85-4 ]

References: [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 342 - 347.

9
[ 63572-73-6 ]
[ 1421428-56-9 ]

References: [1]Patent: WO2013/13816,2013,A1 .
[2]Patent: US2013/29995,2013,A1 .

10
[ 63572-73-6 ]
[ 1421429-85-7 ]

References: [1]Patent: WO2013/13816,2013,A1 .
[2]Patent: US2013/29995,2013,A1 .

11
[ 1820-80-0 ]
[ 34461-00-2 ]
[ 63572-73-6 ]

Yield	Reaction Conditions	Operation in experiment
33%	With hydrogenchloride; zinc(II) chloride; In ethanol; for 1h;Reflux;	1H-pyrazol-3-amine (427 mg, 5.139 mmol) was dissolved in ethanol (10 mL) and 12M HCl (0.5 mL) was added to the stirred solution, followed by granulated zinc chloride (300 mg). The mixture was heated to reflux, and to the mixture was added a solution of 5.139 mmol of the source of the appropriate 1,3-dicarbonyl compound (sodium 2-nitro-1,3-dioxopropan-2-ide) in ethanol (5 mL). After 1 h the reaction mixture was poured into ice-cold water (15 mL), the resultant solution was made alkaline with concentrated aqueous ammonia, and the product was isolated by trichloromethane extraction. The product 5-nitro-1H-pyrazolo[3,4-b]pyridine (279 mg, 33 %) (A) was isolated and purified by column chromatography.

References: [1]Patent: WO2013/13816,2013,A1 .Location in patent: Page/Page column 73.

12
[ 1820-80-0 ]
[ 34461-00-2 ]
[ 63572-73-6 ]

Yield	Reaction Conditions	Operation in experiment
33%		1H-pyrazol-3-amine (427 mg, 5.139 mmol) was dissolved in ethanol (10 mL) and 12M HCl (0.5 mL) was added to the stirred solution, followed by granulated zinc chloride (300 mg). The mixture was heated to reflux, and to the mixture was added a solution of 5.139 mmol of the source of the appropriate 1,3-dicarbonyl compound (sodium 2-nitro-1,3-dioxopropan-2-ide) in ethanol (5 mL). After 1 h the reaction mixture was poured into ice-cold water (15 mL), the resultant solution was made alkaline with concentrated aqueous ammonia, and the product was isolated by trichloromethane extraction. The product 5-nitro-1H-pyrazolo[3,4-b]pyridine (279 mg, 33%) ( A) was isolated and purified by column chromatography.
27%	In water; at 90℃; for 16h;	To a solution of sodium nitromalonaldehyde monohydrate(1.23 g, 7.81 mmol) in water was added 1H-pyrazol-3-amine(0.84 g, 7.43 mmol). The mixture was stirred at 90 C for 16 h andthen cooled to room temperature. The reaction solution wasadjusted to pH 5 and extracted by ethyl acetate (200 mL). Theorganic layer was dried over Na2SO4 and evaporated. The residuewas purified by silica gel chromatography (1% MeOH in dichloromethane)to give 5-nitro-1H-pyrazolo [4,3-b]pyridine as a whitesolid (118 mg, 27%). Rf: 0.23 (DCM/MeOH, 100/1, v/v). Mp:206-208 C. 1H NMR (DMSO-d6, 400 MHz) d 14.40 (s, 1H), 9.35 (d,J 2.5 Hz, 1H), 9.21 (d, J 2.5 Hz, 1H), 8.46 (s, 1H). MS (ESI) m/z:162.8 [MH]-.

References: [1]Patent: US2013/29995,2013,A1 .Location in patent: Paragraph 0372-0373.
[2]European Journal of Medicinal Chemistry,2017,vol. 131,p. 1 - 13.

13
[ 24398-88-7 ]
[ 63572-73-6 ]
C₁₅H₁₄N₄O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2683 - 2687.

14
[ 24398-88-7 ]
[ 63572-73-6 ]
C₁₅H₁₂N₄O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2683 - 2687.

15
[ 63572-73-6 ]
N⁴-(2-(1H-indol-3-yl)ethyl)-6-chloro-N²-(1H-pyrazolo [3,4-b]pyridin-5-yl)quinazoline-2,4-diamine [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 131,p. 1 - 13.

16
[ 63572-73-6 ]
[ 74-88-4 ]
3-iodo-1-methyl-5-nitro-1H-indazole [ No CAS ]

References: [1]Chemical Communications,2017,vol. 53,p. 9446 - 9449.

17
[ 909871-48-3 ]
[ 63572-73-6 ]
2,4-dihydroxy-5-isopropyl-N-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide [ No CAS ]

References: [1]Patent: WO2018/171575,2018,A1 .

18
[ 909871-48-3 ]
[ 63572-73-6 ]
2,4-bis(benzyloxy)-5-isopropyl-N-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide [ No CAS ]

References: [1]Patent: WO2018/171575,2018,A1 .Location in patent: Page/Page column 24; 33; 35; 76.

19
[ 63572-73-6 ]
[ 74-88-4 ]
[ 98157-49-4 ]

References: [1]Patent: WO2018/171575,2018,A1 .Location in patent: Page/Page column 24; 33; 35; 76.

20
[ 21577-50-4 ]
[ 1820-80-0 ]
[ 63572-73-6 ]

References: [1]Patent: WO2018/171575,2018,A1 .Location in patent: Page/Page column 24; 33; 35; 75.

21
[ 63572-73-6 ]
[ 1186609-03-9 ]