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[ CAS No. 1354777-44-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1354777-44-8
Chemical Structure| 1354777-44-8
Chemical Structure| 1354777-44-8
Structure of 1354777-44-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1354777-44-8 ]

CAS No. :1354777-44-8 MDL No. :MFCD20501470
Formula : C7H4BrN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SRLIKUKKKGJCOR-UHFFFAOYSA-N
M.W : 242.03 Pubchem ID :91662762
Synonyms :

Calculated chemistry of [ 1354777-44-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.55
TPSA : 78.87 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.91
Log Po/w (XLOGP3) : 1.31
Log Po/w (WLOGP) : 1.42
Log Po/w (MLOGP) : 1.4
Log Po/w (SILICOS-IT) : 1.57
Consensus Log Po/w : 1.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.61
Solubility : 0.591 mg/ml ; 0.00244 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.656 mg/ml ; 0.00271 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.77
Solubility : 0.41 mg/ml ; 0.00169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 1354777-44-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1354777-44-8 ]

* 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 [ 1354777-44-8 ]

[ 1354777-44-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1248541-63-0 ]
  • [ 1354777-44-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: glacial acetic acid / 0.17 h / 25 °C 1.2: 0.5 h 2.1: lithium hydroxyde monohydrate; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1 h / 25 °C
  • 2
  • [ 1354763-56-6 ]
  • [ 1354777-44-8 ]
YieldReaction ConditionsOperation in experiment
With lithium hydroxyde monohydrate; lithium hydroxide monohydrate In tetrahydrofuran; methanol at 25℃; for 1h; 16.2 Step 2: To a solution of methyl 6-bromo-3H-benzotriazole-4-carboxylate (440 mg, 1.72 mmol) in THF (4 mL), MeOH (2 mL), and H2O (2 mL) was added LiOH•H2O (216.33 mg, 5.16 mmol). The reaction was stirred at 25 °C for 1 hour. The reaction was diluted with water, washed with ethyl acetate, acidified to pH = 2 using HCl (2M), filtered, and the solid was dried under reduced pressure to give 6-bromo-3H-benzotriazole-4- carboxylic acid (450 mg, crude). LCMS (ESI): m/z: [M + H] calculated for C7H5BrN3O2: 241.95; found 241.8;1H NMR (400 MHz, DMSO-d6) δ ppm 16.10 (br s, 1H), 8.64 (s, 1H), 8.10 (s, 1H).
With lithium hydroxyde monohydrate; lithium hydroxide monohydrate In tetrahydrofuran; methanol at 25℃; for 1h; 16.2 Step 2: To a solution of methyl 6-bromo-3H-benzotriazole-4-carboxylate (440 mg, 1.72 mmol) in THF (4 mL), MeOH (2 mL), and H2O (2 mL) was added LiOH•H2O (216.33 mg, 5.16 mmol). The reaction was stirred at 25 °C for 1 hour. The reaction was diluted with water, washed with ethyl acetate, acidified to pH = 2 using HCl (2M), filtered, and the solid was dried under reduced pressure to give 6-bromo-3H-benzotriazole-4- carboxylic acid (450 mg, crude). LCMS (ESI): m/z: [M + H] calculated for C7H5BrN3O2: 241.95; found 241.8;1H NMR (400 MHz, DMSO-d6) δ ppm 16.10 (br s, 1H), 8.64 (s, 1H), 8.10 (s, 1H).
  • 3
  • [ 1354777-44-8 ]
  • [ 2797988-63-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-propanephosphonic acid cyclic anhydride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 25 °C 2: anhydrous sodium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 1,4-dioxane; lithium hydroxide monohydrate / 1 h / 100 °C / Inert atmosphere
  • 4
  • [ 1354777-44-8 ]
  • [ 2797988-29-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1-propanephosphonic acid cyclic anhydride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 25 °C 2: anhydrous sodium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 1,4-dioxane; lithium hydroxide monohydrate / 1 h / 100 °C / Inert atmosphere 3: hydrogenchloride / lithium hydroxide monohydrate; ethyl acetate / 0.5 h / 25 °C
  • 5
  • [ 1389852-29-2 ]
  • [ 1354777-44-8 ]
  • [ 2797988-62-4 ]
YieldReaction ConditionsOperation in experiment
550 mg With 1-propanephosphonic acid cyclic anhydride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; for 1h; 16.3 Step 3: To a solution of 6-bromo-3H-benzotriazole-4-carboxylic acid (430 mg, 1.78 mmol) and (1R)-1-[3-(difluoromethyl)-2-fluoro-phenyl]ethanamine (403 mg, 2.13 mmol) in THF (5 mL) was added T3P (3.17 mL, 5.33 mmol) and DIEA (2.48 mL, 14.21 mmol). The reaction was stirred at 25 °C for 1 hour. The reaction was diluted with water, extracted with ethyl acetate, washed with brine, dried over Na2SO4,filtered, and the solvent was removed under reduced pressure. The residue was purified by column chromatography to give 6-bromo-N-[(1R)-1-[3-(difluoromethyl)-2-fluoro-phenyl]ethyl]- 3H-benzotriazole-4-carboxamide (550 mg, 75% yield). LCMS (ESI): m/z: [M + H] calculated for C16H13BrF3N4O: 413.0; found 412.8;1H NMR (400 MHz, methanol-d4) δ ppm 8.23 (d, J = 33.2 Hz, 2H), 7.51 - 7.68 (m, 2H), 7.30 - 7.32 (m, 1H), 7.02 (t, J = 54.8 Hz, 1H), 5.58 - 5.63 (m, 1H), 1.68 (d, J = 7.2 Hz, 3H).
550 mg With 1-propanephosphonic acid cyclic anhydride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; for 1h; 16.3 Step 3: To a solution of 6-bromo-3H-benzotriazole-4-carboxylic acid (430 mg, 1.78 mmol) and (1R)-1-[3-(difluoromethyl)-2-fluoro-phenyl]ethanamine (403 mg, 2.13 mmol) in THF (5 mL) was added T3P (3.17 mL, 5.33 mmol) and DIEA (2.48 mL, 14.21 mmol). The reaction was stirred at 25 °C for 1 hour. The reaction was diluted with water, extracted with ethyl acetate, washed with brine, dried over Na2SO4,filtered, and the solvent was removed under reduced pressure. The residue was purified by column chromatography to give 6-bromo-N-[(1R)-1-[3-(difluoromethyl)-2-fluoro-phenyl]ethyl]- 3H-benzotriazole-4-carboxamide (550 mg, 75% yield). LCMS (ESI): m/z: [M + H] calculated for C16H13BrF3N4O: 413.0; found 412.8;1H NMR (400 MHz, methanol-d4) δ ppm 8.23 (d, J = 33.2 Hz, 2H), 7.51 - 7.68 (m, 2H), 7.30 - 7.32 (m, 1H), 7.02 (t, J = 54.8 Hz, 1H), 5.58 - 5.63 (m, 1H), 1.68 (d, J = 7.2 Hz, 3H).
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