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[ CAS No. 850568-41-1 ] {[proInfo.proName]}

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2D 3D

Chemical Structure| 850568-41-1

Chemical Structure| 850568-41-1

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Quality Control of [ 850568-41-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 850568-41-1 ]

SDS Specification

Alternatived Products of [ 850568-41-1 ]

Product Details of [ 850568-41-1 ]

CAS No. :	850568-41-1	MDL No. :	MFCD06659818
Formula :	C₉H₁₂BNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZMJVNKSOLIUBKO-UHFFFAOYSA-N
M.W :	193.01	Pubchem ID :	22309454
Synonyms :

Calculated chemistry of [ 850568-41-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	3.0
Molar Refractivity :	53.85
TPSA :	69.56 Å²

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) :	-7.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.06
Log Po/w (WLOGP) :	-1.15
Log Po/w (MLOGP) :	-0.15
Log Po/w (SILICOS-IT) :	-0.84
Consensus Log Po/w :	-0.44

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.05
Solubility :	17.1 mg/ml ; 0.0887 mol/l
Class :	Very soluble
Log S (Ali) :	-0.95
Solubility :	21.7 mg/ml ; 0.112 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.08
Solubility :	1.59 mg/ml ; 0.00824 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.32

Safety of [ 850568-41-1 ]

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

Application In Synthesis of [ 850568-41-1 ]

* 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 [ 850568-41-1 ]

[ 850568-41-1 ] Synthesis Path-Downstream 1~11

1
[ 850568-41-1 ]
[ 950201-38-4 ]
4-(4-(N-acetylmethyl)phenyl)-3-cyano-1-(3-methylbutyl)pyridine-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (4-(acetamidomethyl)phenyl)boronic acid; C₁₂H₁₃F₃N₂O₄S With triethylamine In 1,4-dioxane at 20℃; for 0.0833333h; Stage #2: In 1,4-dioxane at 90℃; for 2h;	B.2 Intermediate compound 4 (150 mg, 0.44 mmol), and 4-(acetamidomethyl)phenyl- boronic acid (129 mg, 0.67 mmol) were mixed in 1,4-dioxane (5 ml) and Et3N (0.12 ml, 0.89 mmol) at room temperature and N2 was flushed through the mixture for 5 min. Pd(PPh3)4 (77 mg, 0.067 mmol) was added and the resulting mixture was heated at 90 0C for 2 hours. The mixture was cooled to room temperature, diluted with AcOEt and brine. The aqueous phase was extracted with AcOEt (3 x 20ml). The combined organ- ics layers were dried over Na2SO4, evaporated in vacuum and the residue thus obtained was purified by column chromatography (SiO2, DCM / AcOEt) to yield 16 mg of final compound 1-179 as a white solid.

Reference： [1]Current Patent Assignee: ADDEX THERAPEUTICS SA; JOHNSON & JOHNSON INC - WO2007/104783, 2007, A2 Location in patent: Page/Page column 57-58

2
[ 850568-41-1 ]
[ 1082066-26-9 ]
[ 1082063-20-4 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: (4-(acetamidomethyl)phenyl)boronic acid; 3'-chloro-4-(1-ethyl-3-methyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl With potassium carbonate In tetrahydrofuran; water for 20h; Heating / reflux; Stage #2: With ammonium chloride In methanol for 0.166667h;	18m Example 18m: N-{4-[4-(l-Ethyl-3-methyl-lH-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro- 2H-[l,2']bipyrazinyl-3'-yl]-benzyl}-acetamide hydrochlorideDissolve 3'-chloro-4-(l-ethyl-3-methyl-lH-pyrazol-4-ylmethyl)-3,4,5,6- tetrahydro-2H-[l,2']bipyrazinyl (0.204 g, 0.636 mmol) in tetrahydrofuran (1.75 mL) and water (0.9 mL). Add potassium carbonate (0.193 g, 1.40 mmol) then 4- acetamidomethylbenzeneboronic acid (0.172 g, 0.890 mmol) and degas with nitrogen for 15 min. Add tri-n-butylphosphine tetrafluoroborate (7.4 mg, 0.0254 mmol) and tris(dibenzylideneacetone)dipalladium(0) (12 mg, 0.0127 mmol) and reflux for 20 hr.Cool to room temperature then dilute with saturated aq. sodium bicarbonate and extract 3 times with ethyl acetate. Dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 4.5:95.5 methanol (with 2 M ammonia):DCM), to give a yellow solid. Dissolve the solid in methanol and add ammonium chloride (1 equivalent) then sonicate the mixture for 10 min. Evaporate the solution to give the title compound as a yellow solid (0.172 g, 51%). MS (ES): m/z [M+H] = 434

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2008/141020, 2008, A1 Location in patent: Page/Page column 171

3
[ 850568-41-1 ]
[ 1123302-10-2 ]
[ 1123301-71-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate In ISOPROPYLAMIDE; water at 110℃; for 18h;	34 Dissolve 1 -methyl- lH-pyrazole-4-sulfonic acid [2-(3'-chloro-2,3,5,6-tetrahydro- [l,2']bipyrazinyl-4-yl)-ethyl]-methyl-amide (200 mg, 0.483 mmol) in DMA-H2O (10 ml; 3: 1 v/v, previously degassed with nitrogen). Add 4-acetamidophenyl boronic acid (112 mg, 0.580 mmol), potassium carbonate (160 mg, 1.16 mmol) and tetrakis(triphenyl- phosphine)palladium (28 mg, 0.024 mmol). Heat the reaction mixture at 1100C for 18 hr. Cool and dilute with ethyl acetate and water. Extract the aqueous layer with ethyl acetate and combine the organic layers. Wash the combined organic layers with brine and concentrate. Purify by chromatography, eluting with 1 :2 hexanes: acetone to afford the free base of the title compound (124 mg, 50 % yield) as a white foam.Prepare the hydrochloride salt by dissolving the free base (124 mg) in acetonitrile and adding IN aqueous HCl (0.266 ml, 0.266 mmol). Stir for 1 hr at ambient > temperature. Remove the organics and lyophilize the remaining aqueous portions to afford the title compound (100% yield). MS ES: m/z = 513 [M+H]+.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2009/29439, 2009, A1 Location in patent: Page/Page column 41-42

4
[ 850568-41-1 ]
[ 1400741-13-0 ]
[ 1400739-80-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate In ethanol; water; toluene at 90℃; for 3h; Inert atmosphere;	2 N-{2-[4'-(Acetylamino-methyl)-biphenyl-4-yI]-l-fluoromethyl-2-hydroxy-ethyl}-2,2- dichloro-acetamide (1-3) A mixture of 13 (300 mg, 0.74 mmol), 4- acetylaminomethylphenylboronic acid (172 mg, 0.89 mmol), K2C03 (306 mg, 2.22 mmol), tetrakis(triphenylphosphine)palladium (0) (41 mg, 0.037 mmol) and toluene/EtOH/H20 (3: 1 : 1 , 10 ml) was degassed. The mixture was heated at 90 °C for 3 h under argonatmosphere. Diluted with EtOAc (30 ml), washed with H20 (20 ml) and concentrated. The crude product was purified by PTLC (EtOAc/Hexane/MeOH, 1 :2:0.3) to afford 1-3 as solid (250 mg, 79%).1NMR (300 MHz, CDC13): δ 7.58 (d, J = 8.1 Hz, 2H), 7.56 (d, J = 8.1 Hz, 2H), 7.45 (d, J = 8.4 Hz, 2H), 7.34 (d, J = 8.4 Hz, 2H), 6.28 (s, 1H), 4.97 (d, J = 3.9 Hz, 1H), 4.62 (ddd, J = 5.3, 9.3, 31.8 Hz, 1H), 4.40 (ddd, J = 4.2, 9.3, 29.4 Hz, 1H), 4.30 (m, 1H);

Reference： [1]Current Patent Assignee: MELINTA THERAPEUTICS INC. - WO2012/125832, 2012, A2 Location in patent: Page/Page column 79-80

5
[ 850568-41-1 ]
[ 591-18-4 ]
C₁₅H₁₄BrNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate In propan-1-ol; water for 18h; Reflux;	2.2 1.3 Method 3 [00314] General conditions for the preparation of 3-bromo-biphenyls: Bromoiodobenzene (1.00 equiv), boronic acid (1.01 equiv), [l,l,-bis(triphenylphosphino)ferrocene]palladium[II] chloride dichloromethane adduct (0.02 equiv) and sodium bicarbonate (3.0 equiv) are combined in 1- propanol/water (4: 1 v:v, 0.3M with respect to iodide). The flask is fitted with a reflux condenser and degassed with vacuum, backfilling with argon, for three cycles. The reaction is heated at reflux overnight and then judged complete by thin layer chromatography or LC/MS, at which point it is cooled, diluted with water, and extracted thrice with ethyl acetate. The combined organic phases are washed with brine, dried over sodium sulfate, and concentrated in vacuo. If needed, the concentrated reaction mixture is purified by flash silica gel chromatography (ethyl acetate/hexanes) to provide the desired 3-bromobiphenyl.

Reference： [1]Current Patent Assignee: INFINITY PHARMACEUTICALS INC - WO2013/49332, 2013, A1 Location in patent: Paragraph 00314

6
[ 850568-41-1 ]
N-(3-bromopyridin-2-yl)-4-methyl-N-(2-methylallyl)benzenesulfonamide [ No CAS ]
N-(4-((3-methyl-1-tosyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)benzyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide Sealed tube; Inert atmosphere; Heating;

Reference： [1]Schempp, Tabitha T.; Daniels, Blake E.; Staben, Steven T.; Stivala, Craig E. [Organic Letters, 2017, vol. 19, # 13, p. 3616 - 3619]

7
[ 850568-41-1 ]
C₁₄H₁₄ClN₅ [ No CAS ]
C₂₃H₂₄N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 4h;

Reference： [1]Gingipalli, Lakshmaiah; Block, Michael H.; Bao, Larry; Cooke, Emma; Dakin, Les A.; Denz, Christopher R.; Ferguson, Andrew D.; Johannes, Jeffrey W.; Larsen, Nicholas A.; Lyne, Paul D.; Pontz, Timothy W.; Wang, Tao; Wu, Xiaoyun; Wu, Allan; Zhang, Hai-Jun; Zheng, Xiaolan; Dowling, James E.; Lamb, Michelle L. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 8, p. 1336 - 1341]

8
[ 850568-41-1 ]
[ 6025-69-0 ]
N-[4-(pyrrolo[1,2-a]quinoxalin-4-yl)benzyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 99℃; for 18h; Inert atmosphere;

Reference： [1]Budke, Brian; Tueckmantel, Werner; Miles, Kelsey; Kozikowski, Alan P.; Connell, Philip P. [ChemMedChem, 2019, vol. 14, # 10, p. 1031 - 1040]

9
[ 850568-41-1 ]
4-chloro-7-(2-fluoroethoxy)pyrrolo[1,2-a]quinoxaline [ No CAS ]
N-[4-[7-(2-fluoroethoxy)pyrrolo[1,2-a]quinoxalin-4-yl]benzyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 99℃; for 18h; Inert atmosphere;

Reference： [1]Budke, Brian; Tueckmantel, Werner; Miles, Kelsey; Kozikowski, Alan P.; Connell, Philip P. [ChemMedChem, 2019, vol. 14, # 10, p. 1031 - 1040]

10
[ 850568-41-1 ]
1-(3-bromo-5-chlorophenyl)cyclobutanecarboximidamide hydrochloride [ No CAS ]
N-((3′-(1-carbamimidoylcyclobutyl)-5′-chloro-[1,1′-biphen-yl]-4-yl)methyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30.4%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium dihydrogenphosphate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere;

Reference： [1]Petros, Andrew M.; Korepanova, Alla; Jakob, Clarissa G.; Qiu, Wei; Panchal, Sanjay C.; Wang, Jie; Dietrich, Justin D.; Brewer, Jason T.; Pohlki, Frauke; Kling, Andreas; Wilcox, Kyle; Lakics, Viktor; Bahnassawy, Lamiaa; Reinhardt, Peter; Partha, Sarathy Karunan; Bodelle, Pierre M.; Lake, Marc; Charych, Erik I.; Stoll, Vincent S.; Sun, Chaohong; Mohler, Eric G. [Journal of Medicinal Chemistry, 2019, vol. 62, # 8, p. 4120 - 4130]

11
[ 850568-41-1 ]
8-((6-bromopyridin-2-yl)(4-methoxybenzyl)amino)-6-(((1R,2R)-2-hydroxycyclohexyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile [ No CAS ]
N-(4-(6-((3-cyano-6-(((1R,2R)-2-hydroxycyclohexyl)amino)imidazo[1,2-b]pyridazin-8-yl)(4-methoxybenzyl)amino)pyridin-2-yl)benzyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54.5%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 100℃; for 12h;	37.2 Step 2 In a 10 mL micro vial 8-((6-bromopyridin-2-yl)(4-methoxybenzyl)amino)-6- (((lR,2R)-2-hydroxycyclohexyl)amino)imidazo[l,2-b]pyridazine-3-carbonitrile (150 mg, 0.274 mmol), (4-(acetamidomethyl)phenyl)boronic acid (63.3 mg, 0.328 mmol), K2CO3 (151 mg, 1.094 mmol) and tetrakis(triphenylphosphine)palladium(0) (22.12 mg, 0.019 mmol) were dissolved in dioxane (3.0 mL) and water (1.0 mL). Then reaction mass was degasified with nitrogen and heated to 100 °C for 12 hours. Then it was submitted to LC- MS. LC-MS showed 36% product formation. The reaction was quenched with water and extracted with ethyl acetate (3 x 5 mL), the combined organic layers were washed with saturated brine, dried over NaiSCri and concentrated. The crude was purified by combi flash 12 gm silica chromatography on elution of 50-60% ethyl acetate: pet ether. Product fractions were combined and concentrated to get N-(4-(6-((3-CN-6-(((lR,2R)-2- hydroxycyclohexyl)amino)imidazo[l,2-b]pyridazin-8-yl)(4-methoxybenzyl)amino) pyridin-2-yl)benzyl)acetamide (100 mg, 0.149 mmol, 54.5 % yield). LC retention time 2.26 min [A] MS (ES+) m/z: 617(MH+).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; BEVERAGE GUIBAO COMPANY - WO2020/180907, 2020, A1 Location in patent: Page/Page column 63; 64

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Ghs Precautionary Statements

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P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
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
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
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
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
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