52090-69-4|5-Methyl-1H-pyrazolo[4,3-b]pyridine| Ambeed

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Quality Control of [ 52090-69-4 ] Purity: 98% SDS Specification

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Product Details of [ 52090-69-4 ]

CAS No. :	52090-69-4
Formula :	C₇H₇N₃
M.W :	133.15
SMILES Code :	CC1=NC2=C(NN=C2)C=C1
MDL No. :	MFCD10696863
InChI Key :	AHRWTDAXNXRLKR-UHFFFAOYSA-N
Pubchem ID :	21300577

Safety of [ 52090-69-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 52090-69-4 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	41.57 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.95
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	0.97
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.27
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.	0.51
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	2.03
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.14

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.94
Solubility	1.52 mg/ml ; 0.0114 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.	-1.43
Solubility	4.94 mg/ml ; 0.0371 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-2.89
Solubility	0.171 mg/ml ; 0.00129 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	Yes
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.	-6.42 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	0.0 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)	1.46

Application In Synthesis of [ 52090-69-4 ]

* 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.

Downstream synthetic route of [ 52090-69-4 ]

[ 52090-69-4 ] Synthesis Path-Downstream 1~21

3
[ 108-24-7 ]
[ 52090-69-4 ]
[ 52090-63-8 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; for 16.0h;	To a solution of N-1 (1 g, 7 mmol) in DCM (5 mL) is added acetic anhydride (1.2 g, 0.01 mol). After 16 hours, the mixture is concentrated and purified by silica gel chromatography eluting with a gradient of 0-70% EtOAc in heptane to provide N-2.

References: [1]Patent: WO2012/87782,2012,A1 .Location in patent: Page/Page column 62.

4
[ 352-34-1 ]
[ 52090-69-4 ]
[ 1383734-99-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;copper(l) iodide; cis-N,N'-dimethyl-1,2-diaminocyclohexane; In N,N-dimethyl-formamide; at 130.0℃; for 1.0h;microwave irradiation;	J-3 (1.50 g, 8.56 mmol) and K2CO3 (1.50 g, 10.9 mmol) in methanol (20 mL) is warmed at reflux for 5 minutes. The mixture is filtered and concentrated to provide J-4. J-4 (1.10 g, 8.26 mmol), Oil (980.0 mg, 5.15 mmol), K2CO3 (2.75 g, 19.9 mmol), N,N- dimethyl-l,2-diaminocyclohexane (150.0 muL, 0.95 mmol) and 4-fluoroiodobenzene (2.40 g, 10.8 mmol) in DMF (13 mL) is warmed at 130C in a microwave reactor. After 1 hour, the reaction is diluted with saturated aqueous NH4C1 (50 mL) and then NaHCO3 is added and the mixture is extracted with EtOAc (3 x 50 mL). The combined organic layers are washed with saturated aqueous NH4C1 (3 x 40 mL), dried over magnesium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 0-50% EtOAc in hexanes and crystallized from ether-hexanes to provide J-6.

References: [1]Patent: WO2012/87782,2012,A1 .Location in patent: Page/Page column 58.

5
[ 3430-33-9 ]
[ 52090-69-4 ]

References: [1]Patent: WO2012/87782,2012,A1 .
[2]Patent: WO2017/133657,2017,A1 .
[3]Patent: WO2017/133667,2017,A1 .

6
[ 51468-08-7 ]
[ 52090-69-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 2-nitropropane; potassium acetate; acetic anhydride; acetic acid; In toluene; at 90.0℃; for 4.0h;	[C] 5-Methyl-1H-pyrazolo [4 3-b] pyridine[0298][0299]To a solution of N- (2 6-dimethylpyridin-3-yl) acetamide (12 g 72.9 mmol) in toluene (200 mL) was added Ac2O (32 mL 292.3 mmol) AcOH (32 mL 485 mmol) and KOAc (19 g 194 mmol) . The misture solution was warmed up to 90 followed by the addition of iPrNO2(16 mL) . The resulting reaction mixture was the stirred at 90 for 4 h. After TLC (MeOHDCM110) showed the reaction was completed the mixture was concentrated under reduced pressure and the residule was re-dissolved in MeOH (200 mL) and added K2CO3(93.7 g 679 mmol) . The mixture was stirred at 90 for another 1 h before cooled back to room temperature. The reaction mixture was filtered and filtrate was concentrated in vacuo to give a crude title compound (2 g 20.5yield) as a solid. MS 134.1 [M+H]+.1HNMR (400MHz CHCl3-d1) delta 13.16 (br. s. 1H) 8.14 (s 1H) 7.89 (d J8.5 Hz 1H) 7.23 (d J8.5 Hz 1H) 2.57 (s 3H) .

References: [1]Patent: WO2012/87782,2012,A1 .
[2]Patent: WO2017/133657,2017,A1 .Location in patent: Page/Page column 67.

7
[ 52090-63-8 ]
[ 52090-69-4 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; potassium carbonate; for 0.08333330000000001h;Reflux;	J-3 (1.50 g, 8.56 mmol) and K2CO3 (1.50 g, 10.9 mmol) in methanol (20 mL) is warmed at reflux for 5 minutes. The mixture is filtered and concentrated to provide J-4.

References: [1]Patent: WO2012/87782,2012,A1 .Location in patent: Page/Page column 57.

8
[ 52090-69-4 ]
[ 1383735-50-9 ]
[ 1383735-51-0 ]