[ CAS No. 368421-58-3 ] {[proInfo.proName]}

Name: 368421-58-3|(2R,3R)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide|97%
Brand: Ambeed
SKU: A401662
Rating: 98 (32 reviews)

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Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 368421-58-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 368421-58-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 368421-58-3 ]

SDS Specification

Alternatived Products of [ 368421-58-3 ]

Product Details of [ 368421-58-3 ]

CAS No. :	368421-58-3	MDL No. :	MFCD28404611
Formula :	C₁₃H₁₄F₂N₄OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UWVOPVUWKIHGRF-ISVAXAHUSA-N
M.W :	312.34	Pubchem ID :	20692784
Synonyms :

Calculated chemistry of [ 368421-58-3 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.31
Num. rotatable bonds :	5
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	76.46
TPSA :	109.05 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) :	-7.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.9
Log Po/w (XLOGP3) :	0.82
Log Po/w (WLOGP) :	2.1
Log Po/w (MLOGP) :	1.58
Log Po/w (SILICOS-IT) :	2.59
Consensus Log Po/w :	1.8

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.35
Solubility :	1.39 mg/ml ; 0.00446 mol/l
Class :	Soluble
Log S (Ali) :	-2.69
Solubility :	0.635 mg/ml ; 0.00203 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.2
Solubility :	0.195 mg/ml ; 0.000625 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.37

Safety of [ 368421-58-3 ]

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

Application In Synthesis of [ 368421-58-3 ]

* 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 [ 368421-58-3 ]

[ 368421-58-3 ] Synthesis Path-Downstream 1~1

1
(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide [ No CAS ]
[ 20099-89-2 ]
[ 241479-67-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydrogencarbonate; In ethanol;	h) Preparation of 4-{2-[(1R,2R)-2-(2,5-Difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-thiazol-4-yl}-benzonitrile A mixture of (2R,3R)-3-(2,5-Difluoro-phenyl)-3-hydroxy-2-methyl-4-[1,2,4]triazol-1-ylthiobutyramide (26.7 g, 85.4 mmol) and a-bromo-4'-cyano-acetophenone (24.0 g, 0.107 mol) in EtOH (500 ml) was refluxed for 1 hr. The reaction mixture was cooled down to r.t. And the solvent was removed under reduced pressure down to 150 ml. The residue was poured into in to cold (0° C.) saturated NaHCO3 aq. (400 ml). The resulting mixture was extracted with EtOAc (300 ml+150 ml*2). The combined organic layer was washed with brine (200 ml), dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel (Wako-gel C-300, Hexane:EtOAc=1:2) to give 4-{2-[(1R,2R)-2-(2,5-Difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-thiazol-4-yl }-benzonitrile (32.0 g, 86percent). Physical form: colorless heavy syrup; ESI-MS: m/z 437 (M)+; 1H-NMR(CDCl3): 1.25(3H,d,J=7.3 Hz),4.12(1 H,q,J=7.3 Hz),4.26,4.96 (2H,Abq,J=14.5 Hz), 5.75(1H,s),6.89~7.07(2H,m),7.23~7.29(1 H,m),7.65 (1H,s),7.71(1H,s),7.75, 8.02(4H,Abq,J=8.6 Hz),7.85(1H,s).
77.4%	In ethanol; at 78℃; for 3h;	The white solid obtained above (3.85 g, 12.75 mmol) was dissolved in absolute ethanol (60 ml), then add alpha-bromo-4-cyanoacetophenone (3.14g, 14.02mmol) to 78°C,The reaction was refluxed for 3 h. After cooling to room temperature, the reaction solution was concentrated and extracted with ethyl acetate.The ethyl acetate phase is washed with saturated sodium bicarbonate solution, the organic phase is dried and concentrated.Ice methyl tert-butyl ether washing, drying white solidIsoconazole4.31g(yield: 77.4percent, e.e. >99percent, d.e. >99percent).
	In ethanol; at 70℃;	In a round bottomed flask charged ethanol (250 ml), thioamide compound (25.0 gm) and 4-cyano phenacyl bromide (18.4 gm) under stirring. The reaction mixture were heated to 70 °C. After completion of reaction the solvent was removed under vacnum distillation and water (250 ml) and Ethyl acetate (350 ml) were added to reaction mass. The reaction mixture was stirred and its pH was adjusted between 7 to 7.5 by 10 percent solution of sodium bicarbonate. The layer aqneous layer was discarded and organic layer was washed with saturated sodium chloride solution (100 ml) and concentrated under vacuum to get residue. The residue was suspended in methyl tert-butyl ether (250 ml) and the reaction mixtnre was heated to at 40°C to make crystals uniform and finally reaction mass is cooled to room temperature filtered and washed with the methyl tert-butyl ether. The product was isolated dried to get pale yellowish solid product.Yield: 26.5 gmHPLC purity: 92.7percent

Reference： [1]Patent: US6300353,2001,B1
[2]Patent: CN106317044,2017,A .Location in patent: Paragraph 0080; 0081
[3]Patent: WO2016/55918,2016,A1 .Location in patent: Page/Page column 15

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Ghs Precautionary Statements

Precautionary Statements-General
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P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
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Code	Phrase
P201	Obtain special instructions before use.
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P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
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.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
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P243	Take precautionary measures against static discharge.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P285	In case of inadequate ventilation wear respiratory protection.
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Response
Code	Phrase
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P304	IF INHALED:
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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P353	Rinse skin with water/shower.
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P372	Explosion risk in case of fire.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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.
P304 + P341	IF INHALED: If breathing is difficult, 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.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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P411 + P235	Keep cool.
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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

[ CAS No. 368421-58-3 ] {[proInfo.proName]}

Quality Control of [ 368421-58-3 ]

Related Doc. of [ 368421-58-3 ]

Product Details of [ 368421-58-3 ]

Calculated chemistry of [ 368421-58-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 368421-58-3 ]

Application In Synthesis of [ 368421-58-3 ]

[ 368421-58-3 ] Synthesis Path-Downstream 1~1

Pharmaceutical Intermediates of [ 368421-58-3 ]

Isavuconazonium Sulfate Related Intermediates

Related Functional Groups of [ 368421-58-3 ]

Fluorinated Building Blocks

Aryls

Alcohols

Amides

Amines

Related Parent Nucleus of [ 368421-58-3 ]

Triazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 368421-58-3 ]

Related Functional Groups of
[ 368421-58-3 ]

Related Parent Nucleus of
[ 368421-58-3 ]