[ CAS No. 444335-16-4 ] {[proInfo.proName]}

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2D 3D

Structure of 444335-16-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 444335-16-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 444335-16-4 ]

SDS Specification

Alternatived Products of [ 444335-16-4 ]

Product Details of [ 444335-16-4 ]

CAS No. :	444335-16-4	MDL No. :	MFCD08166353
Formula :	C₁₀H₉BrFNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UGBKYDASQNOIHP-SSDOTTSWSA-N
M.W :	290.09	Pubchem ID :	34177904
Synonyms :

Calculated chemistry of [ 444335-16-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	61.58
TPSA :	49.77 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.17
Log Po/w (XLOGP3) :	1.63
Log Po/w (WLOGP) :	1.95
Log Po/w (MLOGP) :	1.94
Log Po/w (SILICOS-IT) :	1.89
Consensus Log Po/w :	1.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.81
Solubility :	0.448 mg/ml ; 0.00155 mol/l
Class :	Soluble
Log S (Ali) :	-2.29
Solubility :	1.5 mg/ml ; 0.00515 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.92
Solubility :	0.351 mg/ml ; 0.00121 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.71

Safety of [ 444335-16-4 ]

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 [ 444335-16-4 ]

* 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 [ 444335-16-4 ]
Downstream synthetic route of [ 444335-16-4 ]

[ 444335-16-4 ] Synthesis Path-Upstream 1~3

1
[ 1056039-83-8 ]
[ 444335-16-4 ]
[ 856866-72-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With palladium diacetate; potassium carbonate; triphenylphosphine In 1,4-dioxane at 20℃; Reflux; Inert atmosphere	Under stirring, 1,4-dioxane (400 ml), 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine (20.0 g, 83.3 mmol, 1.0 equiv), bis(pinacolato)diboron (25.3 g, 100 mmol, 1.2 equivalents), potassium acetate (20.4 g, 208 mmol, 2.5 eq) and bis(triphenylphosphine)palladium dichloride (1.17 g, 1.4 mmol, 0.015 eq) was added in sequence to the reaction vessel. The solution was warmed to reflux under nitrogen and TLC followed 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine for complete reaction. After the reaction is completed, it is cooled to below 20 °C. (5R)-3-(4-bromo-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one (21.7 g, 75.0 mmol, 0.9 eq.), potassium carbonate (34.5 g, 250 mmol, 3.0 equiv), palladium acetate (0.14 g, 0.62 mmol, 0.0075 equiv) and triphenylphosphine (0.65 g, 2.5 mmol, 0.03 equiv) was added in sequence to the reaction vessel and nitrogen protected. Warming to reflux, TLC tracks 2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3-dioxoboran-2-yl)pyridine until reaction is complete. After the reaction was completed, it was cooled to room temperature and stirred for 16 hours. It was filtered under reduced pressure and the cake was rinsed with water (200 ml) and methanol (200 ml). The filter cake was collected and air dried at 80° C. to give 25.8 g (compound I) as an off-white powder in a yield of 84percent.
78%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; tricyclohexylphosphine In 1,4-dioxane; water for 4 h; Inert atmosphere; Reflux	At room temperature, 1.0 g of the compound of formula I, 1.2 g of the compound of formula II, 0.8 g of potassium carbonate, 60 mgTricyclohexylphosphine and 72 mg of tris (dibenzylideneacetone) dipalladium (Pd2 (dba) 3) catalyst were added followed by 4 mL of water and 15 mL1,4-dioxane, after a vacuum and nitrogen replacement after heating to reflux, insulation in the reflux state SUZUKI coupling anti-When the SUZUKI coupling reaction was complete (about 4 hours), the reaction was terminated, and the reaction solution was filtered while hot with diatomaceous earth so that the collectedCrystallization of the filtrate naturally cool, l. 0g obtained tidiazolamide crystals (off-white solid), HPLC purity of 99.5percent, the molar yield of 78percent.
63.7%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene for 12 h; Reflux; Inert atmosphere	In 3000 ml of the four port in the round-bottom flask, is provided with the mechanical stirring, reflux condensation tube, thermometer, under the protection of argon is added to the round-bottom flask 1500 ml toluene, 100g (5R) - 3 - (4-bromo-3-fluoro-phenyl) - 5-hydroxy methyl oxazolidine-2-one, 105g2 - (2-methyl -2H-tetrazol-5-yl) pyridine-5-boronic acid frequency ester, 28g two chlorine pairs (triphenyl phosphine) palladium, opening stirring to the solid dissolved, add prepared 140g the potassium carbonate solution dissolving a small amount of water, heating to reflux, the reaction stirred 12 hours, cooling to room temperature. Filtering, the filter cake is washed with water after washing with ethanol mixed solution of methanol used for washing. The filter cake vacuum 45 °C drying 48 hours, shall be 81.3g product. Yield: 63.7percent.

Reference： [1] Patent: CN107382995, 2017, A, . Location in patent: Paragraph 0007; 0014; 0015; 0016; 0117; 0018; 0019-0022
[2] Patent: CN106146485, 2016, A, . Location in patent: Paragraph 0040; 0041; 0042
[3] Patent: CN105418681, 2016, A, . Location in patent: Paragraph 0048; 0049
[4] RSC Advances, 2016, vol. 6, # 63, p. 58088 - 58098

2
[ 444335-16-4 ]
[ 380380-64-3 ]
[ 856866-72-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium acetate; bis(pinacol)diborane In dimethyl sulfoxide at 80℃; for 14 h; Inert atmosphere Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 70℃; for 3 h; Inert atmosphere	DMSO (100 ml) was added to a 250 ml reaction flask,(5R) -3- (4-bromo-3-fluorophenyl) -5-hydroxymethyloxazolidin-2-one(10 g, 34.5 mmol), pinacolate (17.52 g, 69 mmol),[1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium dichloromethane complex (1.41 g, 1.73 mmol)And potassium acetate (13.5 g, 138 mmol), and the temperature was raised to 80 ° C under a nitrogen atmosphere,For 14 hours. The heating was stopped, the solution was cooled to room temperature, and extracted with water / ethyl acetate 3 times. The organic layers were combined and the organic layer was washed with saturated waterBrine, dried over anhydrous sodium sulfate and concentrated by suction filtration. The concentrated product of the above step was added to a 250 ml reaction flask,1,4-dioxane (100 ml) was added,5-bromo-2- (2-methyl-2H-tetrazol-5-yl) pyridine(8.28 g, 34.5 mmol),[1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium dichloromethane complex (0.56 g, 0.69 mmol)And cesium carbonate aqueous solution (50 ml, containing 33.72 g of cesium carbonate, 103.5 mmol),Under nitrogen protection,The temperature was raised to 70 ° C,The reaction was carried out for 3 hours,Dichloromethane was added for extraction.The separated organic phase was washed with saturated brine,Anhydrous sodium sulfate dehydration,filter,Concentrated in vacuo and purified by column chromatography,10.6 g of a solid was obtained,The yield was 83.0percentHPLC purity was 98.34percent (area normalization method).

Reference： [1] Patent: CN105418678, 2016, A, . Location in patent: Paragraph 0070; 0071; 0072; 0073; 0074; 0075

3
[ 444335-16-4 ]
[ 856866-72-3 ]

Reference： [1] Patent: CN107827927, 2018, A,
[2] Patent: CN107827927, 2018, A,

[ 444335-16-4 ] Synthesis Path-Downstream 1~1

1
[ 60827-45-4 ]
[ 288570-67-2 ]
[ 444335-16-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; acetic acid; In tetrahydrofuran; hexane; water; ethyl acetate;	To a solution of 1056 g (3.64 mol) of 2-Methylpropyl (4-bromo-3-fluorophenyl)carbamate in 6.65 L of THF cooled to -15 C. in a 22 L round bottom flask was added a solution of 428 g (4.55 mol, 1.25 equiv.) of lithium t-amylate over 10 min via an addition funnel, maintaining -15 to -12 C. In a separate 5 L flask, a solution of 438 g (4.37 mol, 1.20 equiv.) of (S)-3-chloro-1,2-propanediol in 1.75 L of THF was cooled to -25 C. and treated with a 20% t-BuOK solution in THF (2645 mL, 4.29 mol, 1.18 equiv) over 25 min, resulting in a thick but stirrable slurry. This was allowed to warm to 10 over 75 min and then poured into the 22 L flask containing the carbamate solution. The resulting slurry was allowed to warm from -7 to 7 over 1.5 h, monitoring reaction progress by HPLC. Upon completion (~2.5% each of remaining 2-Methylpropyl (4-bromo-3-fluorophenyl)carbamate and the over addition product) a quench solution composed of 1.05 AcOH and 3.5 L of water was added. The layers were separated. The aqueous layer was back-extracted with 1 L of THF, and the combined organic layers were washed with brine. The volatile were removed, giving white solids wet with acetic acid. This material was slurried in 1.6 L of EtOAc. Hexane (4L) was added over 1 h. The resulting slurry was cooled to 2 over 1 h and filtered, giving 916 g (87%) of (5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one as coarse white crystals: TLC Rf=0.008 (50% EtOAc/hexane); HPLC rt=2.55 min; mp 114-121 ; [alpha]D=+52.2 c. =1, MeOH); 1H NMR (DMSO) delta7.49 (m, 2H), 7.15 (d,1H, J=8.5 Hz), 5.30 (br s, 1H), 4.54 (m,1H), 3.89 (t, 1H, J=8.6 Hz), 3.67 (m, 1H), 3.50 (dd, 1H, J=3.0, 11.8 Hz), 3.39 (dd, 1H, 3.8, 11.8 Hz); 13C NMR (DMSO) delta158.1 (s, JCF=241 hz), 154.2 (S), 139.7 (S, JCF=10 hz), 133.3 (D), 114.9 (D), 105.9 (d, JCF=29 Hz), 100.9 (s, JCF=21 Hz), 73.3(d), 61.5(t), 45.9 (t); Anal. calc'd for C10H9BrFNO3: C, 41.40; H, 3.13; N, 4.83: Br, 27.55; found: C, 41.11; H, 3.06; N, 4.83: Br, 26.97.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4213 - 4216
[2]Patent: US2003/13737,2003,A1

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Appel Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Chugaev Reaction ? Complex Metal Hydride Reductions ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Martin's Sulfurane Dehydrating Reagent ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Preparation of Alcohols ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alcohols ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Ritter Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Swern Oxidation ? Vilsmeier-Haack Reaction

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P422
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

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. 444335-16-4 ] {[proInfo.proName]}

Quality Control of [ 444335-16-4 ]

Related Doc. of [ 444335-16-4 ]

Product Details of [ 444335-16-4 ]

Calculated chemistry of [ 444335-16-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 444335-16-4 ]

Application In Synthesis of [ 444335-16-4 ]

[ 444335-16-4 ] Synthesis Path-Upstream 1~3

[ 444335-16-4 ] Synthesis Path-Downstream 1~1

Technical Information

Related Functional Groups of [ 444335-16-4 ]

Fluorinated Building Blocks

Aryls

Bromides

Alcohols

Amides

Related Parent Nucleus of [ 444335-16-4 ]

Oxazolidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 444335-16-4 ]

Related Parent Nucleus of
[ 444335-16-4 ]