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

Name: 54230-90-9|8-Bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine|95%
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SKU: A193383
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3d Animation Molecule Structure of 54230-90-9

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Quality Control of [ 54230-90-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 54230-90-9 ]

SDS Specification

Alternatived Products of [ 54230-90-9 ]

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 ]

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 Å²

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

Yield	Reaction Conditions	Operation in experiment
	2-Hydrazino-3-brompyridin Xb,Ac2O;

2
[ 1190392-69-8 ]
[ 54230-90-9 ]
[ 1190587-74-6 ]

Yield	Reaction Conditions	Operation 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)+.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2009/253705, 2009, A1 Location in patent: Page/Page column 51

3
[ 1190392-72-3 ]
[ 54230-90-9 ]

Yield	Reaction Conditions	Operation 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)-.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/123870, 2009, A1 Location in patent: Page/Page column 65
[2]Current Patent Assignee: MERCK & CO INC - US2009/253705, 2009, A1 Location in patent: Page/Page column 51

4
[ 1190392-57-4 ]
[ 54230-90-9 ]
[ 1190587-74-6 ]

Yield	Reaction Conditions	Operation 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)+.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/123870, 2009, A1 Location in patent: Page/Page column 65

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 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Current Patent Assignee: RELAY THERAPEUTICS INC - WO2018/81091, 2018, A1 Location in patent: Paragraph 0222

6
[ 13534-89-9 ]
[ 54230-90-9 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/123870, 2009, A1
[2]Current Patent Assignee: MERCK & CO INC - US2009/253705, 2009, A1

7
[ 54231-41-3 ]
[ 54230-90-9 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/123870, 2009, A1

8
[ 54230-90-9 ]
[ 1190392-71-2 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/123870, 2009, A1
[2]Current Patent Assignee: MERCK & CO INC - US2009/253705, 2009, A1

9
[ 54231-41-3 ]
[ 64-19-7 ]
[ 54230-90-9 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2019/149657, 2019, A1 Location in patent: Page/Page column 79; 83; 84

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[ 54230-90-9 ]

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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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H272	May intensify fire; oxidizer
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Health hazards
Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
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H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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H361d	Suspected of damaging the unborn child
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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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

Quality Control of [ 54230-90-9 ]

Related Doc. of [ 54230-90-9 ]

Product Details of [ 54230-90-9 ]

Calculated chemistry of [ 54230-90-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 54230-90-9 ]

Application In Synthesis of [ 54230-90-9 ]

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

Related Functional Groups of [ 54230-90-9 ]

Bromides

Related Parent Nucleus of [ 54230-90-9 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 54230-90-9 ]

Related Parent Nucleus of
[ 54230-90-9 ]