68175-07-5|2-Methyl-1H-imidazo[4,5-b]pyridine| Ambeed

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Quality Control of [ 68175-07-5 ] Purity: 98% SDS Specification

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Product Details of [ 68175-07-5 ]

CAS No. :	68175-07-5
Formula :	C₇H₇N₃
M.W :	133.15
SMILES Code :	CC1=NC2=NC=CC=C2N1
MDL No. :	MFCD03673741
InChI Key :	FZESPVBONPPRAW-UHFFFAOYSA-N
Pubchem ID :	3491069

Safety of [ 68175-07-5 ]

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

Computational Chemistry of [ 68175-07-5 ] 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.	0.84
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	1.15
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.	0.1
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	1.08

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.06
Solubility	1.17 mg/ml ; 0.00879 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.62
Solubility	3.21 mg/ml ; 0.0241 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.	-6.3 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)	1.51

Application In Synthesis of [ 68175-07-5 ]

* 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.

Downstream synthetic route of [ 68175-07-5 ]

[ 68175-07-5 ] Synthesis Path-Downstream 1~21

1
[ 452-58-4 ]
[ 108-24-7 ]
[ 68175-07-5 ]

References: [1]Chemische Berichte,1927,vol. 60,p. 775.
Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1927,vol. 59,p. 417.

2
[ 87888-52-6 ]
[ 68175-07-5 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 1015 - 1018.

3
[ 452-58-4 ]
[ 78-39-7 ]
[ 68175-07-5 ]

References: [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 1719 - 1722.
[2]Tetrahedron Letters,2009,vol. 50,p. 1828 - 1833.
[3]Journal of Chemical Research - Part S,2000,p. 584 - 585.

4
[ 68175-07-5 ]
6-bromo-2-tribromomethylimidazo[4,5-b]pyridine [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 450 - 454.

5
[ 68175-07-5 ]
6-bromo-2-methyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 450 - 454.

6
[ 452-58-4 ]
[ 68175-07-5 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 1015 - 1018.

7
[ 4214-75-9 ]
[ 68175-07-5 ]

References: [1]Chemische Berichte,1927,vol. 60,p. 775.
Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1927,vol. 59,p. 417.

8
[ 68175-07-5 ]
[ 1137089-65-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; at 20℃; for 2.25h;	2-methyl-3H-imidazo[4,5-bjpyridine (10.8 g, 81 mmol) was mixed in EtOAc (500 mL) to give a partial suspension and mCPBA (18.66 g, 81 mmol) was added in portionsover 15 minutes. The resulting mixture was stirred at rt for 1.5 h. LCMS analysis indicated reaction was only 85percent complete, therefore an addition amount of mCPBA (2.2 g) was added. After stirring an additional 30 mm at a, the resulting precipitate which had formed was collected by filtration, rinsed with additional cold EtOAc (50 mL x 3) and dried under vacuum to afford 12 g (99percent) of the desired product as a tan solid.?H NMR (400 MHz, METHANOL-d4): oe 8.24 (dd, J=6.4, 0.7 Hz, 1H), 7.74 (d, J7.9 Hz,1H), 7.31 (dd, J=8.1, 6.4 Hz, 1H), 2.67 (s, 3H).

References: [1]Patent: WO2018/81488,2018,A1 .Location in patent: Page/Page column 42.
[2]Tetrahedron Letters,2009,vol. 50,p. 1828 - 1833.

9
[ 99314-99-5 ]
[ 68175-07-5 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 3798 - 3800.

10
[ 452-58-4 ]
[ 64-19-7 ]
[ 68175-07-5 ]

Yield	Reaction Conditions	Operation in experiment
55.0%		A solution of pyridinediamine (IX), (X), (45.8 mmoles), acetic acid (458.0 mmoles) in PPA (50 ml) was heated to 135-14O0C for 2-4 h under nitrogen atmosphere. After completion of reaction, cooled, transferred the reaction to 250 ml of cold water, charcoal was added and the mixture filtered over a celite bed. The filtrate was basified with aq. ammonia solution till the pH~10-12. Extracted the basified reaction with ethyl acetate (250 ml X3), dried the ethyl acetate layer with sodium sulfate and distilled off the solvent completely to residue. To the residue hexane (50 ml) was added and filtered to get the desired compound (XI and XII). Table 6 : Imdiazopyridines (XI), (XII):

References: [1]Patent: WO2009/137081,2009,A2 .Location in patent: Page/Page column 39-40.

11
[ 495382-05-3 ]
[ 68175-07-5 ]
[ 1195774-61-8 ]

Yield	Reaction Conditions	Operation in experiment
2.5%	With caesium carbonate;copper(I) oxide; 4,7-dimethoxy-1,10-phenanthroline; In dimethyl sulfoxide; at 110 - 115℃; for 24h;	Charged imidazopyridines (XI or XII) (5.115 mmoles), 2-bromo-thiophene-2-carboxamide (VIII) (3.938 mmoles), cesium carbonate (7.161 mmoles), cuprous oxide (0.307 mmoles), 4,7-dimethoxy-l,10-phenathroline (0.716 mmoles), PEG (5.1 15 mmoles) and DMSO to the RB flask fitted with thermo well and condenser. The reaction mass was heated to 110- <n="42"/>1 15 C under magnetic stirring for 24 hours. After completion, it was cooled to room temperature, dichloromethane (500 ml) added and filtered through a celite bed, washed the bed with dichloromethane (100 ml X 2), distilled off the solvent completely under reduced pressure. Aq. ammonia (10 ml) was added and extracted with ethyl acetate (250 ml X 3). Dry the ethyl acetate layer with sodium sulfate, distilled completely to get the crude compound. The crude compound is then purified by using silica gel 60-120 mesh column chromatography and DCM: MeOH 100-5 percent as mobile phase and further by preparative HPLC method to get the pure compounds (XIII, XIV).

References: [1]Patent: WO2009/137081,2009,A2 .Location in patent: Page/Page column 40-41.

12
[ 452-58-4 ]
[ 623-51-8 ]
[ 68175-07-5 ]

References: [1]Chinese Chemical Letters,2010,vol. 21,p. 519 - 523.

13
[ 452-58-4 ]
[ 141-97-9 ]
[ 68175-07-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With gadolinium(III) chloride hexahydrate; at 80℃; for 5h;	General procedure: To a mixture of o-aromatic diamines (200 mg, 1.85 mmol) and 1,3-dicarbonyl compound (722 mg, 5.55 mmol), GdCl3*6H2O (25 mg, 0.09 mmol) was added and the mixture was stirred at 80°C for 3.0 hr. After completion of the reaction (TLC), the reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the corresponding 2-methyl benzimidazole. The crude material was further purified by through column chromatography by using 10percent ethyl acetate in hexane.

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2015,vol. 54B,p. 953 - 957.

14
[ 68175-07-5 ]
N₅-(5-fluoropyridin-2-yl)-2-methyl-N₇-(2-(methylsulfonyl)phenyl)-3H-imidazo[4,5-b]pyridine-5,7-diamine [ No CAS ]