[ CAS No. 1012881-37-6 ] {[proInfo.proName]}

Name: 1012881-37-6|Ethyl 2-(tert-butyl)thiazole-5-carboxylate|97%
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3d Animation Molecule Structure of 1012881-37-6

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Quality Control of [ 1012881-37-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1012881-37-6 ]

SDS Specification

Alternatived Products of [ 1012881-37-6 ]

Product Details of [ 1012881-37-6 ]

CAS No. :	1012881-37-6	MDL No. :	MFCD28137670
Formula :	C₁₀H₁₅NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KZJMIYNMRNUMFW-UHFFFAOYSA-N
M.W :	213.30	Pubchem ID :	58790083
Synonyms :

Calculated chemistry of [ 1012881-37-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.6
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	57.47
TPSA :	67.43 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.79
Log Po/w (XLOGP3) :	3.21
Log Po/w (WLOGP) :	2.62
Log Po/w (MLOGP) :	1.33
Log Po/w (SILICOS-IT) :	3.38
Consensus Log Po/w :	2.67

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.19
Solubility :	0.139 mg/ml ; 0.000653 mol/l
Class :	Soluble
Log S (Ali) :	-4.3
Solubility :	0.0107 mg/ml ; 0.0000503 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.99
Solubility :	0.217 mg/ml ; 0.00102 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.84

Safety of [ 1012881-37-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1012881-37-6 ]

* 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 [ 1012881-37-6 ]

[ 1012881-37-6 ] Synthesis Path-Downstream 1~5

1
[ 70-23-5 ]
[ 630-22-8 ]
2-tert-butyl thiazole-5-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.0%	In ethanol; at 20℃; for 48h;	A solution of ethyl 3-bromopyruvate (1.95 g, 10 mmol, 1.0 eq) and 2, 2, 2-trimethyl-thioacetamide (1.17 g, 10 mmol, 1.0 eq) in 20 mL of ethanol was stirred at room temperature for 48 h. The solvent was evaporated under reduced pressure, and the residue was extracted with aqueous sodium bicarbonate and DCM. The DCM layer was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was separated by column chromatography to give 2-tert-butyl-thiazole-5-carboxylic acid ethyl ester as a colorless oil (1.15 g, 55.0% yield). 1H NMR (400 MHz, CDCl3) delta 8.01 (s, 1H), 4.38 (q, J=7.1 Hz, 2H), 1.46 (s, 9H), 1.37 (t, J=7.1 Hz, 3H). MS m/z (ESI): 214.0 [M+H].

Reference： [1]Patent: US2017/305920,2017,A1 .Location in patent: Paragraph 0185; 0186

2
[ 1012881-37-6 ]
[ 1012881-39-8 ]

Yield	Reaction Conditions	Operation in experiment
55%	With lithium hydroxide monohydrate In tetrahydrofuran at 20℃; for 16h;	16.2 Preparation of 2-tert-butyl-thiazole-5-carboxylic acid To a 2-tert-butyl-thiazole-5-carboxylate in 10 mL of THF, 5 mL of lithium hydroxide (0.45 g, 10.9 mmol, 1.1 eq) aqueous solution was added and the obtained solution was stirred at room temperature for about 16 h. The solvent was evaporated under reduced pressure, and the residue was dissolved in 5 mL of water. The pH was adjusted to about 3 with 2M HCl, and a large amount of white flocculent solid was precipitated. The filter cake was washed with water (2×5 mL) to give 2-Tert-butyl-thiazole-5-carboxylic acid as a white solid (0.55 g, 55.0% yield). MS m/z (ESI): 184.0 [M-H].
	With ethanol; lithium hydroxide monohydrate; sodium hydroxide at 20℃; for 5h;	180 Ethyl 2-tert-butylthiazole-5-carboxylate (350 mg, 1.64 mmol, 1 eq) in methanol (1 mL) was saponified under standard conditions using added sodium hydroxide (6 M, 1 mL, 3.66 eq) to provide the carboxylic acid intermediate (150 mg, crude) as a white solid.

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY; ST CHUAN UNIV - US2017/305920, 2017, A1 Location in patent: Paragraph 0187
[2]Current Patent Assignee: PMV PHARMACEUTICALS INC - WO2021/231474, 2021, A1 Location in patent: Paragraph 0937-0938

3
[ 1012881-37-6 ]
[ 1970150-77-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium hydroxide / tetrahydrofuran / 16 h / 20 °C 2: thionyl chloride / 2 h / 80 °C

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY; ST CHUAN UNIV - US2017/305920, 2017, A1

4
[ 1012881-37-6 ]
[ 1970150-78-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / tetrahydrofuran / 16 h / 20 °C 2: thionyl chloride / 2 h / 80 °C 3: ammonium chloride; triethylamine / dichloromethane / 0.17 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: SICHUAN UNIVERSITY; ST CHUAN UNIV - US2017/305920, 2017, A1

5
[ 630-22-8 ]
[ 33142-21-1 ]
[ 1012881-37-6 ]

Yield	Reaction Conditions	Operation in experiment
64.1%	With toluene-4-sulfonic acid; glacial acetic acid at 110℃; for 12h;	180 EXAMPLE 180: Compound 437B: 2-tert-butyl-N-[3-(4-[(3S,4R)-3-fluoro-1-methylpiperidin-4- yl]amino}-1-(2,2,2-trifluoroethyl)-1H-indol-2-yl)-1,2,4-oxadiazol-5-yl]methyl}-1,3-thiazole-5- carboxamide To a mixture of 2,2-dimethylpropanethioamide (300 mg, 2.56 mmol, 1 eq) and ethyl 2-chloro-3- oxo-propanoate (404.6 mg, 2.69 mmol, 1.05 eq) in acetic acid (3 mL) was added 4- methylbenzenesulfonic acid hydrate (97.4 mg, 512 μmol, 0.2 eq). The mixture was stirred at 110 °C for 12 h. The residue was poured into ice-water (w/w = 1/1) (100 mL). The aqueous phase was extracted with EA (20 mLx3). The combined organic phase was washed with brine (20 mLx3), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by prep-TLC (SiO2, PE: EA=5:1) to afford the thaizole product (350 mg, 64.1% yield) as a light yellow oil. LC-MS (ES+, m/z):214.0 [(M+H)+].1H NMR (400 MHz, CHLOROFORM-d) δ = 8.27 (s, 1H), 4.35 (q, J=7.15 Hz, 2H), 1.46 (s, 9H), 1.37 (t, J=7.15 Hz, 3H).
64.1%	With toluene-4-sulfonic acid; glacial acetic acid at 110℃; for 12h;	180 EXAMPLE 180: Compound 437B: 2-tert-butyl-N-[3-(4-[(3S,4R)-3-fluoro-1-methylpiperidin-4- yl]amino}-1-(2,2,2-trifluoroethyl)-1H-indol-2-yl)-1,2,4-oxadiazol-5-yl]methyl}-1,3-thiazole-5- carboxamide To a mixture of 2,2-dimethylpropanethioamide (300 mg, 2.56 mmol, 1 eq) and ethyl 2-chloro-3- oxo-propanoate (404.6 mg, 2.69 mmol, 1.05 eq) in acetic acid (3 mL) was added 4- methylbenzenesulfonic acid hydrate (97.4 mg, 512 μmol, 0.2 eq). The mixture was stirred at 110 °C for 12 h. The residue was poured into ice-water (w/w = 1/1) (100 mL). The aqueous phase was extracted with EA (20 mLx3). The combined organic phase was washed with brine (20 mLx3), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by prep-TLC (SiO2, PE: EA=5:1) to afford the thaizole product (350 mg, 64.1% yield) as a light yellow oil. LC-MS (ES+, m/z):214.0 [(M+H)+].1H NMR (400 MHz, CHLOROFORM-d) δ = 8.27 (s, 1H), 4.35 (q, J=7.15 Hz, 2H), 1.46 (s, 9H), 1.37 (t, J=7.15 Hz, 3H).

Reference： [1]Current Patent Assignee: PMV PHARMACEUTICALS INC - WO2021/231474, 2021, A1 Location in patent: Paragraph 0937
[2]Current Patent Assignee: PMV PHARMACEUTICALS INC - WO2021/231474, 2021, A1 Location in patent: Paragraph 0937

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Isomers

Technical Information

• Acyl Group Substitution • Alcohols Convert Acyl Chlorides into Esters • Alcoholysis of Anhydrides • Amines Convert Esters into Amides • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Complex Metal Hydride Reductions • Convert Esters into Aldehydes Using a Milder Reducing Agent • Decarboxylation of 3-Ketoacids Yields Ketones • Deprotection of Cbz-Amino Acids • Ester Cleavage • Ester Hydrolysis • Grignard Reagents Transform Esters into Alcohols • Hantzsch Pyridine Synthesis • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Specialized Acylation Reagents-Carbodiimides and Related Reagents • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • Transesterification

Historical Records

Related Functional Groups of
[ 1012881-37-6 ]

Esters

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Methyl 2-(tert-butyl)thiazole-5-carboxylate

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Methyl 2-cyclopropylthiazole-5-carboxylate

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Related Parent Nucleus of
[ 1012881-37-6 ]

Thiazoles

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P222	Do not allow contact with air.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
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.
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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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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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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. 1012881-37-6 ] {[proInfo.proName]}

Quality Control of [ 1012881-37-6 ]

Related Doc. of [ 1012881-37-6 ]

Product Details of [ 1012881-37-6 ]

Calculated chemistry of [ 1012881-37-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1012881-37-6 ]

Application In Synthesis of [ 1012881-37-6 ]

[ 1012881-37-6 ] Synthesis Path-Downstream 1~5

Technical Information

Related Functional Groups of [ 1012881-37-6 ]

Esters

Related Parent Nucleus of [ 1012881-37-6 ]

Thiazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1012881-37-6 ]

Related Parent Nucleus of
[ 1012881-37-6 ]