305381-67-3|1-Methyl-1H-benzo[d][1,2,3]triazole-5-carboxylic acid| Ambeed

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Quality Control of [ 305381-67-3 ] Purity: 95% SDS Specification

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Product Details of [ 305381-67-3 ]

CAS No. :	305381-67-3
Formula :	C₈H₇N₃O₂
M.W :	177.16
SMILES Code :	CN1N=NC2=CC(=CC=C12)C(O)=O
MDL No. :	MFCD03086163
InChI Key :	SGHWYTLJLHVIBQ-UHFFFAOYSA-N
Pubchem ID :	2776549

Safety of [ 305381-67-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Computational Chemistry of [ 305381-67-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	45.75
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	68.01 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.15
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	0.66
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.67
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.	0.97
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	0.28
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.74

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.8
Solubility	2.8 mg/ml ; 0.0158 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.	-1.66
Solubility	3.84 mg/ml ; 0.0217 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	-1.47
Solubility	5.98 mg/ml ; 0.0337 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	No
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.	-6.91 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.	0.56

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)	1.66

Application In Synthesis of [ 305381-67-3 ]

* 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 [ 305381-67-3 ]

[ 305381-67-3 ] Synthesis Path-Downstream 1~18

1
1.3-dimethyl-5-carboxy-benztriazolium chloride [ No CAS ]
[ 305381-67-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1896,vol. 291,p. 336.

2
[ 66315-15-9 ]
[ 305381-67-3 ]

Yield	Reaction Conditions	Operation in experiment
79%	With acetic acid; sodium nitrite; In water; at 0℃; for 24h;	Step 3. 1-Methyl-1H-benzo[d][1,2,3]triazole-5-carboxylic acid To a solution of 3-amino-4-(methylamino)benzoic acid (8 g, 48.1 mmol) in 5% AcOH (300 ml) was added a solution of sodium nitrite (3.9 g, 56.93 mmol) in water, dropwise with stirring at 0 C. The resulting solution was stirred for 24 hours at 0 C. The solids were collected by filtration to afford 1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylic acid as a white solid (6.7 g, 79%). LC/MS (ES, m/z): [M+H]+. 178.1 1H-NMR (300 MHz, DMSO) δ 13.16 (s, 1H), 8.60 (s, 1H), 8.09-8.12 (m, 1H), 7.93 (d, J=8.7 Hz, 1H), 4.35 (s, 3H)
18%		Step 1: 1-METHYL-LH-BENZO [d] [1, 2,3] triazole-5-carboxylic acid (284) [0440] To a stirred suspension of the diamine 280 (1.08g ; 6. 48MMOL) (or any other o- arylenediamine) in water (25 mL) at 0C, concentrated HCI (5.4 mL) was added drop wise followed by slow addition of a solution of NAN02 (643mg; 9. 3mmol) in water (10 mL). The reaction mixture was stirred at 0C for 2h and then was allowed to warm up to 10C over 4h; neutralized with a solution of KOH (5.6 g) in water (30mL) (final pH = 6); concentrated and purified by preparative HPLC in reverse phase mode (column aquasil C-18, elution 5% to 95% MeOH in water), to afford the title compound 284 (211 mg; 18% YIELD). 1H NMR: (400.2 MHz, DMSO) 5 (ppm): 8.35 (s; 1H); 8.08 (dd, J= 1. 4,8. 6 Hz; 1H); 7.75 (d, J= 1.4 Hz; 1H); 4.03 (s, 3H). MS: calc : 177.1 ; found: 178.1 (M+H).

References: [1]Patent: US2012/277224,2012,A1 .Location in patent: Page/Page column 41.
[2]Patent: WO2005/30704,2005,A1 .Location in patent: Page/Page column 246.

3
[ 305381-67-3 ]
[ 504-02-9 ]
[ 305381-87-7 ]

Yield	Reaction Conditions	Operation in experiment
1.35 g (59%)	With 1,2-dichloro-ethane; triethylamine;	1.1 Cyclohexen-3-on-1-yl 1-methylbenzotriazole-5-carboxylate 1.5 g of 1-methylbenzotriazole-5-carboxylic acid (8.5 mmol) and 1.0g of 1,3-cyclohexanedione (8.9 mmol) were dissolved in 30 ml of abs. acetonitrile and admixed with 1.6 g of EDC (8.5 mmol), 2 ml of triethylamine and a cat. amount of DMAP. After the reaction had ended, the solution was poured into water and extracted with ethyl acetate. The organic phase was washed and dried and the product was then purified by crystallization. Yield: 1.35 g (59%). m.p.: 154-158 C.

References: [1]Patent: US6589915,2003,B1 .

4
[ 305381-67-3 ]
[ 33641-15-5 ]
[ 306276-95-9 ]

Yield	Reaction Conditions	Operation in experiment
0.77 g (35%)	With 1,2-dichloro-ethane; triethylamine;dmap;	5.1 1-Methylpyrazol-5-yl 1-Methylbenzotriazole-5-carboxylate 1.5 g of 1-methylbenzotriazole-5-carboxylic acid (8.5 mmol) and 0.87 g of 1-methyl-5-hydroxypyrazole (8.9 mmol) were dissolved in 70 ml of abs. acetonitrile and admixed with 1.62 g of EDC (8.5 mmol), 2 ml of triethylamine and a catalytic amount of DMAP. After the reaction had ended, the solution was poured into water and the mixture was extracted with ethyl acetate. The organic phase was washed and dried, and the product was then purified by crystallization. Yield: 0.77 g (35%). 1H NMR (CDCl3, TMS): δ=3.82 (s, 3H); 4.40 (s, 3H); 6.28 (d, 1H); 7.48 (d, 1H); 7.67 (d, 1H); 8.36 (d, 1H); 8.98 (s, 1H) ppm.

References: [1]Patent: US6541423,2003,B1 .

5
[ 453-71-4 ]
[ 305381-67-3 ]

References: [1]Patent: US2012/277224,2012,A1 .

6
[ 305381-67-3 ]
[ 1404449-29-1 ]

References: [1]Patent: US2012/277224,2012,A1 .

7
[ 41263-74-5 ]
[ 305381-67-3 ]

References: [1]Patent: US2012/277224,2012,A1 .
[2]Chinese Chemical Letters,2017,vol. 28,p. 919 - 926.

8
[ 2033-24-1 ]
[ 305381-67-3 ]
[ 1404449-28-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 24h;	Step 4. 2,2-Dimethyl-5-(1-methyl-1H-1,2,3-benzotriazole-5-carbonyl)-1,3-dioxane-4,6-dione A solution of <strong>[305381-67-3]1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylic acid</strong> (1 g, 5.64 mmol), EDC HCl (1.61 g, 10.37 mmol), 4-dimethylaminopyridine (1.44 g, 11.79 mmol), and 2,2-dimethyl-1,3-dioxane-4,6-dione (970 mg, 6.73 mmol) in dichloromethane (30 ml) was stirred for 24 hours at room temperature. The resulting solution was washed with HCl (3N), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford 2,2-dimethyl-5-(1-methyl-1H-1,2,3-benzotriazole-5-carbonyl)-1,3-dioxane-4,6-dione as a white solid (1.4 g, crude).

References: [1]Patent: US2012/277224,2012,A1 .Location in patent: Page/Page column 41.

9
[ 36242-50-9 ]
[ 305381-67-3 ]