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[ CAS No. 305381-67-3 ] {[proInfo.proName]}

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Chemical Structure| 305381-67-3
Chemical Structure| 305381-67-3
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Product Details of [ 305381-67-3 ]

CAS No. :305381-67-3 MDL No. :MFCD03086163
Formula : C8H7N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SGHWYTLJLHVIBQ-UHFFFAOYSA-N
M.W : 177.16 Pubchem ID :2776549
Synonyms :

Calculated chemistry of [ 305381-67-3 ]      Expand+

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 : 68.01 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.15
Log Po/w (XLOGP3) : 0.66
Log Po/w (WLOGP) : 0.67
Log Po/w (MLOGP) : 0.97
Log Po/w (SILICOS-IT) : 0.28
Consensus Log Po/w : 0.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.8
Solubility : 2.8 mg/ml ; 0.0158 mol/l
Class : Very soluble
Log S (Ali) : -1.66
Solubility : 3.84 mg/ml ; 0.0217 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.47
Solubility : 5.98 mg/ml ; 0.0337 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 305381-67-3 ]

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

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 ]
  • 2
  • [ 66315-15-9 ]
  • [ 305381-67-3 ]
YieldReaction ConditionsOperation in experiment
79% With acetic acid; sodium nitrite; In water; at 0℃; for 24.0h; Step 3.1-Methyl-1H-benzo[d][1,2,3]triazole-5-carboxylic acidTo a solution of <strong>[66315-15-9]3-amino-4-(methylamino)benzoic acid</strong> (8 g, 48.1 mmol) in 5percent 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, 79percent).LC/MS (ES, m/z): [M+H]+. 178.11H-NMR (300 MHz, DMSO) delta 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 0°C, 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 0°C for 2h and then was allowed to warm up to 10°C 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 5percent to 95percent MeOH in water), to afford the title compound 284 (211 mg; 18percent 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).
  • 3
  • [ 305381-67-3 ]
  • [ 504-02-9 ]
  • [ 305381-87-7 ]
YieldReaction ConditionsOperation 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.
  • 4
  • [ 305381-67-3 ]
  • [ 33641-15-5 ]
  • [ 306276-95-9 ]
YieldReaction ConditionsOperation 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 <strong>[33641-15-5]1-methyl-5-hydroxypyrazole</strong> (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): delta=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.
  • 5
  • [ 453-71-4 ]
  • [ 305381-67-3 ]
  • 6
  • [ 305381-67-3 ]
  • [ 1404449-29-1 ]
  • 8
  • [ 2033-24-1 ]
  • [ 305381-67-3 ]
  • [ 1404449-28-0 ]
YieldReaction ConditionsOperation 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).
  • 9
  • [ 36242-50-9 ]
  • [ 305381-67-3 ]
  • 10
  • [ 66315-16-0 ]
  • [ 305381-67-3 ]
  • 11
  • methyl 1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylate [ No CAS ]
  • [ 305381-67-3 ]
YieldReaction ConditionsOperation in experiment
53% With sodium hydroxide; In water; at 40℃; for 4h; 1 g (4.8 mmol) s4 was suspended in 20 mL water, 20 mL NaOH (2N) aqueous solution was added. The mixture was heated and maintained at 40C for 4 h, cooled, neutralized with HCl (2mol/L) and extracted with 50 mL ethyl acetate. The filtrate was concentrated by vacuum distillation to obtain brown solid of s5500 mg, yield 53%. MS calcd. for: C8H7N3O2: 177.05, GC/MS: 177.
  • 12
  • [ 305381-67-3 ]
  • methyl 1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylate [ No CAS ]
  • 13
  • [ 305381-67-3 ]
  • ethyl 1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylate [ No CAS ]
  • 14
  • [ 305381-67-3 ]
  • trifluoroethyl 1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylate [ No CAS ]
  • 15
  • [ 305381-67-3 ]
  • 2-(2-hydroxybenzoyloxy)-ethyl-1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylate [ No CAS ]
  • 16
  • [ 305381-67-3 ]
  • 2-(4-chlorobenzoyloxy)-ethyl-1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylate [ No CAS ]
  • 17
  • [ 305381-67-3 ]
  • [ 423768-38-1 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; In dichloromethane; at 20℃; for 1h; 100 mg (0.56 mmol) s5 was suspended in 5 mL CH2Cl2, 0.5 mL (0.27 mmol) oxalyl chloride was added slowly. The mixture was stirred at room temperature for 1 h. Solvent was removed by vacuum distillation, the residue was dissolved in 5 mL CH2Cl2 and added dropwise to a mixture containing 0.6 mmol ethanol, 1.8 mmol triethylamine and 5 mL CH2Cl2. The mixture was stirred at room temperature for another 5 h. Then, the solvent was removed by vacuum distillation, the residue was recrystallized from ethyl acetate and hexane to give white solid 3b 65 mg. Yield44%. mp 104-105C. 1H NMR(400 MHz, CDCl 3 ): d 8.80 (s, 1H, ArH),8.20 (d, 1H, J = 8.4 Hz, ArH), 7.55 (d, 1H, J = 8.8 Hz, ArH), 4.44 (q, 2H,J = 7.2 Hz, OCH 2 ), 4.34 (s, 3H, NCH 3 ), 1.44 (t, 3H, J = 7.2 Hz, CH 3 );13CNMR (100 MHz, CDCl 3 ): d166.1, 145.7, 135.6, 128.2, 126.6, 122.8,108.9, 61.4, 34.4, 14.3. HRMS (ESI) calcd. for C 10 H 11 N 3 O 2 [M+H]+:205.0851, found 205.0850.
  • 18
  • [ 305381-67-3 ]
  • N2-((1R,4R)-4-aminocyclohexyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methylpyrimidine-2,4-diamine [ No CAS ]
  • N-((1R,4R)-4-((4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrimidin-2-yl)(methyl)amino)cyclohexyl)-1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% To a solution of <strong>[305381-67-3]1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylic acid</strong> (162.2 mg, 0.916 mmol) in dry DMF (6 mL) was added TEA (0.38 mL, 2.752 mmol) followed by EDC.HCl (262 mg, 1.376 mmol) and HOBt (124 mg, 0.916 mmol). The reaction mixture was stirred at room temperature for 10 min, and then N2-((1R,4R)-4-aminocyclohexyl)-N4-(5- cyclopropyl-1H-pyrazol-3-yl)-N2-methylpyrimidine-2,4-diamine (300 mg, 0.916 mmol) was added. The reaction mixture was stirred at room temperature for 16 h. After completion of the reaction, reaction mixture was diluted with dichloromethane washed with water and brine, dried over anhydrous Na2SO4 and concentrated to yield the crude product. The crude product was purified by reverse phase prep HPLC to provide N-((1R,4R)-4-((4-((5-cyclopropyl-1H- pyrazol-3-yl)amino)pyrimidin-2-yl)(methyl)amino)cyclohexyl)-1-methyl-1H- benzo[d][1,2,3]triazole-5-carboxamide (45 mg, 10%) as the free base. LC purity: 99.34%; m/z: 487.3 [M+H]+ (Mol. formula C25H30N10O, calcd. mol. wt. 486.58).1H VTNMR (400MHz, CD3OD): δ 8.50 (s, 1H), 8.06 (dd, J = 8.8, 8.4 Hz, 1H), 7.89 (d, J = 5.6 Hz, 1H), 7.82 (d, J = 8.8 Hz, 1H), 6.15-6.13 (m, 2H), 4.57 -4.62 (m, 1H), 4.37 (s, 3H), 3.97-3.89 (m, 1H), 3.05 (s, 3H), 2.21-2.18 (m, 2H), 1.95 - 1.82 (m, 5H), 1.72-1.65 (m, 2H), 1.00-0.96 (m, 2H), 0.77-0.73 (m, 2H).
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