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[ CAS No. 54230-90-9 ] {[proInfo.proName]}

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Chemical Structure| 54230-90-9
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Product Details of [ 54230-90-9 ]

CAS No. :54230-90-9 MDL No. :MFCD15144595
Formula : C7H6BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :DWOFCCIXSLDUSD-UHFFFAOYSA-N
M.W : 212.05 Pubchem ID :66924502
Synonyms :

Calculated chemistry of [ 54230-90-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.65
TPSA : 30.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.73
Log Po/w (XLOGP3) : 2.27
Log Po/w (WLOGP) : 1.8
Log Po/w (MLOGP) : 1.82
Log Po/w (SILICOS-IT) : 1.58
Consensus Log Po/w : 1.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.19
Solubility : 0.137 mg/ml ; 0.000645 mol/l
Class : Soluble
Log S (Ali) : -2.54
Solubility : 0.61 mg/ml ; 0.00288 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.233 mg/ml ; 0.0011 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 54230-90-9 ]

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

Application In Synthesis of [ 54230-90-9 ]

* 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 [ 54230-90-9 ]

[ 54230-90-9 ] Synthesis Path-Downstream   1~9

YieldReaction ConditionsOperation in experiment
2-Hydrazino-3-brompyridin Xb,Ac2O;
  • 2
  • [ 1190392-69-8 ]
  • [ 54230-90-9 ]
  • [ 1190587-74-6 ]
YieldReaction ConditionsOperation in experiment
73% With copper(l) chloride In tetrahydrofuran at 60℃; for 6h; 64.C To a solution of 0.13 g (0.61 mmol) of 8-bromo-3-methyl[1,2,4]triazolo[4,3-a]pyridine from Step B above in 4 mL of anhydrous THF was added a solution of 0.36 g (0.80 mmol) of benzyl 2-(tributylstannyl)acrylate (see Intermediate 62, Step B) in 1 mL of anhydrous THF, 0.11 g (0.09 mmol) of tetrakis(triphenylphosphine)palladium(0) and 0.067 g (0.67 mmol) of copper (I) chloride. The reaction mixture was heated to 60° C. for 6 h, cooled and filtered through a pad of Celite. The pad was washed with 15 mL of a dichloromethane and the combined filtrates were evaporated to dryness. The crude residue was purified by silica gel chromatography eluting with a 0-6% methanol in ethyl acetate gradient to afford the title compound (0.13 g, 73%). LC-MS: m/z (ES) 294 (MH)+.
  • 3
  • [ 1190392-72-3 ]
  • [ 54230-90-9 ]
YieldReaction ConditionsOperation in experiment
84% With acetic acid In toluene for 20h; Reflux; Dean-Stark trap; 64.B To a solution of 0.17 g (0.74 mmol) of N-(3-bromopyridJn-2-yl)acetohydrazide from step A in 40 mL of anhydrous toluene was added 3 mL of glacial acetic acid and the resulting mixture was heated to reflux for 20 h employing a Dean-Stark trap. The reaction mixture was cooled to ambient temperature then evaporated to dryness in vacuo to afford the title compound (0.13 g, 84%) LC-MS : m/z (ES) 212, 214 (MH)+.
84% With acetic acid In toluene for 20h; Reflux; 64.B To a solution of 0.17 g (0.74 mmol) of N'-(3-bromopyridin-2-yl)acetohydrazide from step A above in 40 mL of anhydrous toluene was added 3 mL of glacial acetic acid and the resulting mixture was heated to reflux for 20 h employing a Dean-Stark trap. The reaction mixture was cooled to ambient temperature then evaporated to dryness in vacuo to afford the title compound (0.13 g, 84%) LC-MS: m/z (ES) 212, 214 (MH)-.
  • 4
  • [ 1190392-57-4 ]
  • [ 54230-90-9 ]
  • [ 1190587-74-6 ]
YieldReaction ConditionsOperation in experiment
73% With copper(l) iodide In tetrahydrofuran at 60℃; for 6h; 64.C To a solution of 0.13 g (0.61 mmol) of 8-bromo-3-methyl[1,2,4jtriazolo[4,3- αjpyridine from Step B in 4 mL of anhydrous THF was added a solution of 0.36 g (0.80 mmol) of benzyl 2-(tributylstannyl)acrylate (see Intermediate 62, Step B) in 1 mL of anhydrous THF,0.11 g (0.09 mmol) of tetrakis(triphenylphosphine)palladium(0) and 0.067 g (0.67 mmol) of copper (1) chloride. The reaction mixture was heated to 60'C for 6 h, cooled and filtered through a pad of Celite. The pad was washed with 15 mL of a dichloromethane and the combined filtrates were evaporated to dryness. The crude residue was purified by silica gel chromatography eluting with a 0-6% methanol in ethyl acetate gradient to afford the title compound (0λ3 g, 73%). LC-MS: m/z (ES) 294 (MH)+.
  • 5
  • 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroquinoline [ No CAS ]
  • [ 54230-90-9 ]
  • 5-(3-methyl-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-1,2,3,4-tetrahydroquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 95℃; for 3h; 2 Step 2 5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)-1 ,2,3,4-tetrahydroquinoline (100 mg, 0.3858 mmol), 8-bromo-3-methyl-[ 1 ,2,4jtriazolo[4,3 -aj pyridine (63 mg, 0.2967 mmol), tetrakis(triphenylphosphine)Palladium (34 mg, 0.02967 mmol), and potassium carbonate (82 mg, 0.5935 mmol) were dissolved in dioxane (4 mL) and water (1 mL) and stirred at 95 °C for 3 h. The mixture was cooled to room temperature and partitionedbetween water and ethyl acetate. Following separation of the layers, , the organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. The cmde residue was purified by silica gel chromatography (eluting with 0-100% ethyl acetate in heptanes). Product- containing fractions were combined and concentrated in vacuo to give 5-(3-methyl- [1 ,2,4jtriazolo[4,3-ajpyridin-8-yl)-1 ,2,3,4-tetrahydroquinoline (31.8 mg, 0.1203 mmol, 41%yield).
  • 6
  • [ 13534-89-9 ]
  • [ 54230-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine / 1,4-dioxane / 8 h / 85 °C 2: triethylamine / dichloromethane / 0.33 h / -78 - 20 °C 3: acetic acid / toluene / 20 h / Reflux; Dean-Stark trap
Multi-step reaction with 2 steps 1.1: hydrazine / 1,4-dioxane / 8 h / 85 °C 1.2: 0.33 h / -78 - 20 °C / Inert atmosphere 2.1: acetic acid / toluene / 20 h / Reflux
  • 7
  • [ 54231-41-3 ]
  • [ 54230-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0.33 h / -78 - 20 °C 2: acetic acid / toluene / 20 h / Reflux; Dean-Stark trap
  • 8
  • [ 54230-90-9 ]
  • [ 1190392-71-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide / tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 6 h / 60 °C 2: hydrogen / palladium 10% on activated carbon / methanol / 6 h / 760.05 Torr
Multi-step reaction with 2 steps 1: copper(l) chloride / tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 6 h / 60 °C 2: hydrogen / palladium 10% on activated carbon / methanol / 6 h / 760.05 Torr
  • 9
  • [ 54231-41-3 ]
  • [ 64-19-7 ]
  • [ 54230-90-9 ]
YieldReaction ConditionsOperation in experiment
340 g Reflux; 4 8-bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine Intermediate 4.9a 3-Bromo-2-hydrazinylpyridine (350 mg; 1.9 mmol) is dissolved in 2 ml_ of acetic acid. The mixture is heated to reflux over night. The mixture is concen- trated. The mixture is filtered before being purified by reverse phase chromato- graphy-HPLC (modifier: trifluoroacetic acid). The product is dissolved in dichloro- methane and washed with a saturated aqueous solution of sodium bicarbonate. The organic phase is dried by being run through a phase separator cartridge and concentrated.Yield: 340 g (85 % of theory)Mass spectrometry (ESI+): m/z = 212/214 [M+H]+HPLC (Method 3): Retention time = 0.591 min.
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