[ CAS No. 182556-72-5 ]

Name: 182556-72-5|4-(Benzyloxy)-2-chloropyridine|97%
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SKU: A316363
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Quality Control of [ 182556-72-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 182556-72-5 ]

SDS Specification

Alternatived Products of [ 182556-72-5 ]

Product Details of [ 182556-72-5 ]

CAS No. :	182556-72-5	MDL No. :	MFCD11847315
Formula :	C₁₂H₁₀ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XZLZQERVHJHMAL-UHFFFAOYSA-N
M.W :	219.67	Pubchem ID :	53404197
Synonyms :

Calculated chemistry of [ 182556-72-5 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.08
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	60.23
TPSA :	22.12 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.58
Log Po/w (XLOGP3) :	3.28
Log Po/w (WLOGP) :	3.16
Log Po/w (MLOGP) :	2.29
Log Po/w (SILICOS-IT) :	3.49
Consensus Log Po/w :	2.96

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.66
Solubility :	0.0478 mg/ml ; 0.000218 mol/l
Class :	Soluble
Log S (Ali) :	-3.42
Solubility :	0.0836 mg/ml ; 0.000381 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.31
Solubility :	0.00108 mg/ml ; 0.0000049 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.8

Safety of [ 182556-72-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 182556-72-5 ]

* 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.

Upstream synthesis route of [ 182556-72-5 ]
Downstream synthetic route of [ 182556-72-5 ]

[ 182556-72-5 ] Synthesis Path-Upstream 1~1

1
[ 182556-72-5 ]
[ 85333-26-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With lithium hexamethyldisilazane In tetrahydrofuran at 65℃; for 0.5 h;	Example 10 ; [Show Image] Synthesis of N4-(4-(H-imidazo[1,2-a]pyridin-7-yloxy)-3-methylphenyl)-N6-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)quinazoline-4,6-diamine Step A: Preparation of 4-(benzyloxy)pyridin-2-amine: To a mixture of 4-(benzyloxy)-2-chloropyridine (1.10 g, 5.01 mmol), Pd₂dba₃ (46 mg, 0.05 mmol) and 2-(dicyclohexylphosphino)-2',4',6'-tri-propyl-1,1'-biphenyl (57 mg, 0.120 mmol) in THF (10 mL) was added LHMDS (6 mL of 1.0 M solution). After heating to 65 °C for 30 minutes, the mixture was cooled to room temperature and concentrated onto silica gel. The product was eluted with 20:1 ethyl acetate/methanol to isolate a pale gold solid (0.97 g, 96percent).
82%	Stage #1: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium hexamethyldisilazane; CyJohnPhos In tetrahydrofuran at 65℃; for 1 h; Inert atmosphere Stage #2: With hydrogenchloride; water In tetrahydrofuran for 0.0833333 h;	LiHMDS (105.4 mL, 1 M solution in THF, 105.4 mmol) was added to a solution of intermediate 10 ( 19.3 g, 87.9 mmol), Pd₂(dba).5 (2.0 g, 2.2 mmol, 0.025 eq.) and 2- dicyclohexylphosphinobiphenyl (2.5 g, 5.2 mmol, 0.06 eq.) in anhydrous THF (90 mL) under a nitrogen atmosphere, the resulting mixture was stirred at 65 °C for 1 h. The reaction was then allowed to cool to room temperature and IN aqueous HC1 was added. Following 5 min of vigorous stirring, the reaction mixture was neutralized with saturated Na2CC"3 and extracted with CH2CI2. The combined organic phases were dried over MgS04 and concentrated under reduced pressure. The crude product was suspended in isopropyl ether and stirred for 15 min at reflux temperature, after which it was allowed to cool to room temperature overnight. The precipitate was filtered off and dried under high vacuum to give intermediate 11 ( 14.7 g, 82percent yield).
70.2%	Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at 50℃; for 1.5 h; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 2 h;	Example 195 3-(5-bromo-2-C4-phenethylthiazol-2-ylamino)pyridin-4-yloxyV5- chloroisonicotinonitrile[00552] Step A: Preparation of ^fbenzyloxVlp yridiα-2-amine: A-(benzyloxy)-2-chloroρyridine (18.6 g, 84.7 mmol), XPHOS (4.04 g₅ 8.47 mmol), and Pd₂dba₃ (3.88 g, 4.23 mmol) were mixed in THF (250 mL). LHMDS (93.1 ml, 93.1 mmol) was added and the reaction was heated at 50 ⁰C for 1.5 hours. The solution was cooled and diluted with IN HCl (50 mL) and stirred at ambient temperature for 2 hours. The reaction was concentrated and the residue was extracted with EtOAc. The aqueous layer was basified with saturated K₂CO₃ and the aqueous layer was extracted with EtOAc. The combined organic layers were dried and concentrated to give the desired product (11.9 g, 70.2percent yield) as a brown solid.

Reference： [1] Patent: EP2090575, 2009, A1, . Location in patent: Page/Page column 54-55
[2] Patent: WO2018/65365, 2018, A1, . Location in patent: Page/Page column 114-115
[3] Patent: WO2007/89512, 2007, A1, . Location in patent: Page/Page column 181

[ 182556-72-5 ] Synthesis Path-Downstream 1~5

1
[ 182556-72-5 ]
[ 85333-26-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With lithium hexamethyldisilazane;tris-(dibenzylideneacetone)dipalladium(0); 2-(dicyclohexylphosphino)-2',4',6'-tri-1-propyl-1,1'-biphenyl; In tetrahydrofuran; at 65℃; for 0.5h;	Example 10 ; [Show Image] Synthesis of N4-(4-(H-imidazo[1,2-a]pyridin-7-yloxy)-3-methylphenyl)-N6-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)quinazoline-4,6-diamine Step A: Preparation of 4-(benzyloxy)pyridin-2-amine: To a mixture of 4-(benzyloxy)-2-chloropyridine (1.10 g, 5.01 mmol), Pd2dba3 (46 mg, 0.05 mmol) and 2-(dicyclohexylphosphino)-2',4',6'-tri-propyl-1,1'-biphenyl (57 mg, 0.120 mmol) in THF (10 mL) was added LHMDS (6 mL of 1.0 M solution). After heating to 65 C for 30 minutes, the mixture was cooled to room temperature and concentrated onto silica gel. The product was eluted with 20:1 ethyl acetate/methanol to isolate a pale gold solid (0.97 g, 96%).
82%		LiHMDS (105.4 mL, 1 M solution in THF, 105.4 mmol) was added to a solution of intermediate 10 ( 19.3 g, 87.9 mmol), Pd2(dba).5 (2.0 g, 2.2 mmol, 0.025 eq.) and 2- dicyclohexylphosphinobiphenyl (2.5 g, 5.2 mmol, 0.06 eq.) in anhydrous THF (90 mL) under a nitrogen atmosphere, the resulting mixture was stirred at 65 C for 1 h. The reaction was then allowed to cool to room temperature and IN aqueous HC1 was added. Following 5 min of vigorous stirring, the reaction mixture was neutralized with saturated Na2CC"3 and extracted with CH2CI2. The combined organic phases were dried over MgS04 and concentrated under reduced pressure. The crude product was suspended in isopropyl ether and stirred for 15 min at reflux temperature, after which it was allowed to cool to room temperature overnight. The precipitate was filtered off and dried under high vacuum to give intermediate 11 ( 14.7 g, 82% yield).
70.2%		Example 195 3-(5-bromo-2-C4-phenethylthiazol-2-ylamino)pyridin-4-yloxyV5- chloroisonicotinonitrile[00552] Step A: Preparation of ^fbenzyloxVlp yridialpha-2-amine: A-(benzyloxy)-2-chlororhoyridine (18.6 g, 84.7 mmol), XPHOS (4.04 g5 8.47 mmol), and Pd2dba3 (3.88 g, 4.23 mmol) were mixed in THF (250 mL). LHMDS (93.1 ml, 93.1 mmol) was added and the reaction was heated at 50 0C for 1.5 hours. The solution was cooled and diluted with IN HCl (50 mL) and stirred at ambient temperature for 2 hours. The reaction was concentrated and the residue was extracted with EtOAc. The aqueous layer was basified with saturated K2CO3 and the aqueous layer was extracted with EtOAc. The combined organic layers were dried and concentrated to give the desired product (11.9 g, 70.2% yield) as a brown solid.

Reference： [1]Patent: EP2090575,2009,A1 .Location in patent: Page/Page column 54-55
[2]Patent: WO2019/214634,2019,A1 .Location in patent: Page/Page column 70; 71; 72
[3]Patent: WO2018/65365,2018,A1 .Location in patent: Page/Page column 114-115
[4]Patent: WO2007/89512,2007,A1 .Location in patent: Page/Page column 181

2
[ 1603-91-4 ]
[ 182556-72-5 ]
[ 945988-39-6 ]

Yield	Reaction Conditions	Operation in experiment
47.5%	With potassium phosphate In water; toluene at 90℃;	1.B Step B: Preparation of 4-rbenzyloxyVN-('4-methylthiazol-2- yDpyridin-2-amine: A 250 mL round-bottomed flask was charged with 2- amino-4-methylthiazole (43.8 mL, 17.5 mmol), 4-(benzyloxy)-2-chloroρyridine (4.23 g, 19.3 mmol), potassium phosphate (4.09 g, 19.3 mmol), and toluene (44 mL), and the reaction mixture was degassed with nitrogen. Tris(dibenzylideneacetone)-dipalladium (0) (0.401 g, 0.438 mmol) and 9,9- dimethyl-4,5-bis(diphenyl-phosphino)-xanthene (0.279 g, 0.482 mmol) were added, and the reaction mixture was degassed with nitrogen. The reaction mixture was warmed to 90 0C, degassed water (15 mL) was added, and reaction mixture was stirred at 90 0C overnight. Water was added, and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered through a small plug of silica gel, and the filtrate was concentrated down to 50 mL of ethyl acetate and filtered to afford 4- (benzyloxy)-iV-(4-methylthiazol-2-yl)pyridin-2-amine (2.50 g, 47.5% yield) as a white solid. 1H NMR (CDCl3) δ 9.29 (bs, IH), 8.15 (d, IH), 7.39 (m, 4H), 7.35 (m, IH), 6.53 (dd, IH), 6.41 (d, IH), 6.36 (d, IH), 5.07 (s. 2H), 2.33 (s, 3H). Mass spectrum (esi) m/z = 298 (M

Reference： [1]Current Patent Assignee: PFIZER INC - WO2007/89512, 2007, A1 Location in patent: Page/Page column 80

3
[ 53937-02-3 ]
[ 182556-72-5 ]

Yield	Reaction Conditions	Operation in experiment
47.1%		Example 1 2-f2-f4-Methylthiazol-2-ylamino)pyridin-4-yloxy)berizom'trile[00330] Step A: Preparation of 4-fbenzyloxyV2-chloropyridine: A 250 mL round-bottomed flask was charged with 4-(benzyloxy)pyridin-2(lH)-one (10.0 g, 49.7 mmol) and phosphorus oxychloride (55.6 mL, 596 mmol). The reaction mixture was heated at 90 0C overnight, then cooled and carefully quenched with sodium carbonate and sodium hydroxide to pH 7. The aqueous layer was extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography with dichloromethane as eluent to afford 4- (benzyloxy)-2-chloropyridine (5.14 g, 47.1% yield) as white solid. 1H NMR <n="81"/>(CDCl3) delta 8.19 (d, IH), 7.34-7.44 (m, 5H), 6.91 (d, IH)5 6.81 (dd, IH), 5.10 (s, 2H). LC/MS: (5 to 95) R, = 2.64 min (ESI) m/z = 220 (M+H) (40%).

Reference： [1]Patent: WO2007/89512,2007,A1 .Location in patent: Page/Page column 79-80

4
[ 26452-80-2 ]
[ 100-51-6 ]
[ 182556-72-5 ]

Yield	Reaction Conditions	Operation in experiment
52%	Stage #1: benzyl alcohol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,4-dichloropyridine In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	A.6.1 Step 1 (1497) Preparation of intermediate 10 A solution of benzyl alcohol (18.2 g, 168 mmol, 1.0 eq.) in DMF (100 mL) was added dropwise to suspension of NaH (60% dispersion in mineral oil, 6.5 g, 168 mmol, 1.0 eq.) in DMF (300 mL) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for an extra 30 minutes. A solution of 2,4-dichloropyridine (24.9 g, 168 mmol, 1.0 eq.) in DMF (100 mL) was added dropwise. The reaction mixture was stirred for 2 h, after which an additional portion of NaH (60% dispersion in mineral oil, 1.3 g, 33.6 mmol, 0.2 eq.) was added. Stirring was continued until complete conversion. Upon completion, the reaction mixture was quenched by the slow addition of water, and extracted with diethyl ether. The combined organic phases were dried with MgS04 and concentrated under reduced pressure. The crude product was suspended in heptane, filtered and dried under high vacuum to give intermediate 10 ( 19.3 g, 52% yield).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2018/65365, 2018, A1 Location in patent: Page/Page column 114

5
[ 34941-91-8 ]
[ 100-51-6 ]
[ 182556-72-5 ]

Yield	Reaction Conditions	Operation in experiment
84.1%	Stage #1: benzylic alcohol With sodium hydride In 1,4-dioxane at 60℃; for 2h; Stage #2: 2-chloro-4-fluoropyridine In 1,4-dioxane for 3h; Reflux;
78%	Stage #1: benzylic alcohol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 2-chloro-4-fluoropyridine In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Inert atmosphere;	s18.1 Step 1: Synthesis of 4-(benzyloxy)-2-chloropyridine. To a solution of benzyl alcohol (8.2 g, 76.03 mmol) in DMF (50.0 mL) was added NaH (3.7 g, 60%) at 0°C under N2. The mixture was stirred at 0°C for 20 min under N2. Then 2-chloro-4-fluoropyridine (10.0 g, 76.03 mmol) was added to the mixture. The mixture was stirred at room temperature for another 1 h. After the reaction was completed, the resulting mixture was diluted with H2O and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by flash column chromatography with petroleum ether/ethyl acetate (50/50, v/v) to afford 4-(benzyloxy)-2-chloropyridine (13.0 g, 78%) as a white solid. LCMS (ESI, m/z): [M+H]+ =220.0.
78%	Stage #1: benzylic alcohol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 2-chloro-4-fluoropyridine In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Inert atmosphere;	s18.1 Step 1: Synthesis of 4-(benzyloxy)-2-chloropyridine. To a solution of benzyl alcohol (8.2 g, 76.03 mmol) in DMF (50.0 mL) was added NaH (3.7 g, 60%) at 0°C under N2. The mixture was stirred at 0°C for 20 min under N2. Then 2-chloro-4-fluoropyridine (10.0 g, 76.03 mmol) was added to the mixture. The mixture was stirred at room temperature for another 1 h. After the reaction was completed, the resulting mixture was diluted with H2O and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by flash column chromatography with petroleum ether/ethyl acetate (50/50, v/v) to afford 4-(benzyloxy)-2-chloropyridine (13.0 g, 78%) as a white solid. LCMS (ESI, m/z): [M+H]+ =220.0.

71%

Stage #1: benzylic alcohol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.333333h; Stage #2: 2-chloro-4-fluoropyridine In N,N-dimethyl-formamide; mineral oil at 90 - 100℃;

Reference： [1]Current Patent Assignee: DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD. - WO2019/214634, 2019, A1 Location in patent: Page/Page column 70; 71
[2]Current Patent Assignee: ENLIVEN THERAPEUTICS - WO2022/6386, 2022, A1 Location in patent: Paragraph 0397-0398
[3]Current Patent Assignee: ENLIVEN THERAPEUTICS - WO2022/6386, 2022, A1 Location in patent: Paragraph 0397-0398
[4]Ogasawara, Daisuke; Ichu, Taka-Aki; Jing, Hui; Hulce, Jonathan J.; Reed, Alex; Ulanovskaya, Olesya A.; Cravatt, Benjamin F. [Journal of Medicinal Chemistry, 2019, vol. 62, # 3, p. 1643 - 1656]

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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

[ CAS No. 182556-72-5 ]

Quality Control of [ 182556-72-5 ]

Related Doc. of [ 182556-72-5 ]

Product Details of [ 182556-72-5 ]

Calculated chemistry of [ 182556-72-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 182556-72-5 ]

Application In Synthesis of [ 182556-72-5 ]

[ 182556-72-5 ] Synthesis Path-Upstream 1~1

[ 182556-72-5 ] Synthesis Path-Downstream 1~5

Precautionary Statements-General

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Physical hazards

Health hazards

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