[ CAS No. 473927-64-9 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 473927-64-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 473927-64-9 ]

SDS Specification

Alternatived Products of [ 473927-64-9 ]

Product Details of [ 473927-64-9 ]

CAS No. :	473927-64-9	MDL No. :	MFCD19442850
Formula :	C₂₂H₂₀IN₃O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DOONVRNBSUAOKN-UHFFFAOYSA-N
M.W :	517.32	Pubchem ID :	22240493
Synonyms :

Calculated chemistry of [ 473927-64-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	30
Num. arom. heavy atoms :	17
Fraction Csp3 :	0.23
Num. rotatable bonds :	6
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	123.76
TPSA :	73.66 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.7
Log Po/w (XLOGP3) :	4.45
Log Po/w (WLOGP) :	3.48
Log Po/w (MLOGP) :	3.46
Log Po/w (SILICOS-IT) :	3.86
Consensus Log Po/w :	3.79

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.87
Solubility :	0.000691 mg/ml ; 0.00000134 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.72
Solubility :	0.000995 mg/ml ; 0.00000192 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.86
Solubility :	0.0000714 mg/ml ; 0.000000138 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.38

Safety of [ 473927-64-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 473927-64-9 ]

* 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 [ 473927-64-9 ]

[ 473927-64-9 ] Synthesis Path-Downstream 1~3

1
[ 1415831-80-9 ]
[ 27143-07-3 ]
[ 473927-64-9 ]

Yield	Reaction Conditions	Operation in experiment
63%		Example 4. Synthesis of a compound of formula (II): l-(4- methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-l//- pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl esterIII IV IICompound (IV) (0.82 g, 3.19 mmol) is dissolved in 5 ml of AcOEt in a ml 3-necked flask equipped with coolant, thermometer and magnetic stirrer, in nitrogen atmosphere, and cooled to 0° with an ice bath. Compound (III) (1.02 g, 2.63 mmol) and triethylamine (0.89 ml, 6.40 mmol) are added. When the additions have been completed, the reaction is heated to reflux temperature for 3h, after which another portion of compound (IV) (350 mg) and triethylamine (0.25 ml) are added. When compound (III) has completely disappeared, the end-of-reaction mixture is cooled to 0°C, treated with a solution of HC1 (1.80 g of 37percent HC1 in 3.20 g of H2O) and maintained under stirring at room temperature overnight. A solid precipitates, which is filtered through a Buchner funnel and washed with 5 ml of a 1 : 1 solution of AcOEt and isopropanol. The compound of formula (II) is obtained as a solid (0.85 g, yield 63percent).1H NMR (300 MHz, CDC13): 67.67 (2H, dd, J0=8.7 Hz, Ar-H), 7.46 (2H, dd, Jo=9.0 Hz, Ar-H), 7.06 (2H, dd, Jo=9.0 Hz, Ar-H), 6.90 (2H, dd, Jo=9.0 Hz, Ar-H), 4.45 (2H, q, J=7.2 Hz, 4.09 (2H, t, J=6.6 Hz, CH2(3/4N), 3.81 (3H, s, Ar-OCH3), 3.32 (2H, t, J=6.6 Hz, (3/4CH2N), 1.43 (3H, t, J=7.3 Hz, COOCH2CH3).

Reference： [1]Patent: WO2012/168364,2012,A1 .Location in patent: Page/Page column 17-18

2
[ 473927-69-4 ]
[ 27143-07-3 ]
[ 473927-64-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine; In ethyl acetate; at 0℃; for 2h;Inert atmosphere; Cooling with ice; Reflux;	The preparation was carried out in an inert atmosphere (argon). 2-Chloro-2-[2-(4- methoxyphenyl)hydrazono] acetic acid ethyl ester (14.1 g; 0.055 mol) was dissolved in 140 ml of ethyl acetate. The solution was cooled to 0-5°C in an iced water bath. The solution being stirred, 1-(4-iodophenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one (21.1 g; 0.055 mol) was added in portions. After stirring up, triethylamine (11.1 g; 0.110 mol) was added dropwise to the reaction mixture at 0-5 °C. The cooling of the reaction mixture was interrupted and the temperature was left to rise to the room level. Then, heating was started up to reflux. The reflux temperature of the reaction mixture was maintained for ca. 120 min. Completion of the reaction was monitored by means of HPLC. The reaction mixture was cooled to 0-5°C again and concentrated hydrochloric acid (27.5 ml; 0.275 mol) diluted with distilled water in the 1 :1 ratio was slowly added dropwise. Being cooled, the reaction mixture was stirred for ca. 1 h. Then, another 55 ml of water was added and the resulting suspension was stirred for another 2 h while being cooled. The separated product was isolated by filtration and dried in vacuo at 50°C for 24 h. The product III was obtained in the yield of 21.3 g; i.e. 75 percent and HPLC quality of 95 percent.
30.4%		Step-2: Ethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H- pyrazolo [3,4-cJ pyridine-3-carboxylate 1 -(4-Iodophenyl)-3 -morpholine-5,6-dihydro-2H-pyridin-2-one (100 g, obtained in step-i), <strong>[27143-07-3]ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate</strong> (100 g) and triethylamine (131.6g) were added to toluene (1000 ml) at room temperature. The resulting mixture was heated to reflux and then stirred for 2 hours at reflux. The reaction mass was cooled to room temperature, followed by filtration and then washing with toluene (50 ml x 2). The resulting toluene layer was washed with water (200 ml x 2), followed by distillation of toluene layer under vacuum at 90°C to obtain a residue (164 g). 4N Hydrochloric acid (79.2g) and dichloromethane (315 ml) were added to the resulting residue and then stirred for 2 hours at room temperature. The reaction mass was washed with 2percent sodium bicarbonate solution (200 ml), followed by washing with water (200 ml) and then adjusting the pH to 6. The resulting dichioromethane layer was treated with carbon (10 g), followed by distillation under vacuum at 55°C to obtain a residue (175 g). Acetone (200 ml) was addedto the resulting residue and then stirred for 30 minutes at room temperature. The resulting mass was cooled to 0-5°C for 30 minutes and then stirred for 30 minutes. The separated solid was filtered, washed with chilled acetone (70 ml) and then dried the material at 65°C for 3 hours to produce 102 g of ethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7- tetrahydro- 1 H-pyrazolo[3 ,4-c]pyridine-3 -carboxylate (Purity by HPLC: 99percent; overall yield:30.4percent).

Reference： [1]Patent: WO2014/75648,2014,A1 .Location in patent: Page/Page column 11
[2]Patent: WO2015/177801,2015,A1 .Location in patent: Page/Page column 23

3
3-chloro-5,6-dihydro-1-(4-iodophenyl)-piperidin-2-one [ No CAS ]
[ 27143-07-3 ]
[ 473927-64-9 ]

Yield	Reaction Conditions	Operation in experiment
109 g	With triethylamine; In toluene; for 2h;Reflux;	Example 6Preparation of ethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro- 1H-pyrazolo[3,4-cJ pyridine-3-carboxylate3-Chloro-5,6-dihydro-1-(4-iodophenyl)-piperidin-2-one (100 g, obtained in example 4), ethyl 2-chloro-2-(2.-(4-methoxyphenyl)hydrazono)acetate (115 g, obtained in example 5)and triethylamine (151.5 g) were added to toluene (1000 ml) at room temperature and the mixture was heated to reflux. The resulting mass was stirred for 2 hours at reflux, followed by filtration and then washing with toluene (200 ml). The resulting toluene layer was washed with water (200 ml x 2) and then subjected to carbon treatment. The resulting organic layer was distilled under vacuum to obtain a residue. Acetone (150 ml) was addedto the resulting residue and then stirred for 30 minutes at room temperature. The reaction mass was then cooled to 0-5°C, followed by stirring the mass for 30 minutes at the same temperature. The separated solid was filtered, washed with acetone (30 ml) and then dried the material at 65°C for 3 hours to produce 109 g of ethyl 6-(4-iodophenyl)-1-(4- methoxyphenyl)-7-oxo-4,5 ,6,7-tetrahydro- 1 H-pyrazolo[3 ,4-c}pyridine-3 -carboxylate(Purity by HPLC: 99percent; melting range: 171.2°C to 173°C).

Reference： [1]Patent: WO2015/177801,2015,A1 .Location in patent: Page/Page column 26

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Ester Cleavage ? Friedel-Crafts Reaction ? General Reactivity ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Lawesson's Reagent ? Nomenclature of Ethers ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Ethers ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions of Ethers ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

Historical Records

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[ 473927-64-9 ]

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1-(4-Iodophenyl)piperidin-2-one

[ 536759-91-8 ]

Ethyl 1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate

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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

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

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[ CAS No. 473927-64-9 ] {[proInfo.proName]}

Quality Control of [ 473927-64-9 ]

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Calculated chemistry of [ 473927-64-9 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

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[ 473927-64-9 ] Synthesis Path-Downstream 1~3

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Apixaban Related Intermediates

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Aryls

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Other Aromatic Heterocycles

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[ 473927-64-9 ]

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[ 473927-64-9 ]

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[ 473927-64-9 ]