[ CAS No. 259654-73-4 ] {[proInfo.proName]}

Name: 259654-73-4|Methyl 2-(2-amino-5-methylthiazol-4-yl)acetate|97%
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SKU: A187967
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3d Animation Molecule Structure of 259654-73-4

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Quality Control of [ 259654-73-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 259654-73-4 ]

SDS Specification

Alternatived Products of [ 259654-73-4 ]

Product Details of [ 259654-73-4 ]

CAS No. :	259654-73-4	MDL No. :	MFCD00662517
Formula :	C₇H₁₀N₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	186.23	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 259654-73-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.43
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.35
TPSA :	93.45 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) :	-6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.63
Log Po/w (XLOGP3) :	0.83
Log Po/w (WLOGP) :	0.76
Log Po/w (MLOGP) :	-0.07
Log Po/w (SILICOS-IT) :	1.95
Consensus Log Po/w :	1.02

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.63
Solubility :	4.39 mg/ml ; 0.0236 mol/l
Class :	Very soluble
Log S (Ali) :	-2.37
Solubility :	0.785 mg/ml ; 0.00422 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.8
Solubility :	2.92 mg/ml ; 0.0157 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.44

Safety of [ 259654-73-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H320-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 259654-73-4 ]

* 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 [ 259654-73-4 ]
Downstream synthetic route of [ 259654-73-4 ]

[ 259654-73-4 ] Synthesis Path-Upstream 1~3

1
[ 259654-73-4 ]
[ 496062-16-9 ]

Reference： [1] Patent: US2018/153859, 2018, A1,

2
[ 17356-08-0 ]
[ 105983-77-5 ]
[ 259654-73-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	at 100℃; for 1 h;	To a solution of bromide from Step 1 (18 g, 86 [MMOL)] in toluene (100 mL) was added thiourea (10.5 g, 138 [MMOL).] The reaction mixture was heated to [100C] for 1 h, cooled to rt, and the solvent removed under reduced pressure. The residue was dissolved in [CH2CI2] (100 mL), a saturated solution of [NAHC03] (75 mL) was added, and the mixture was vigorously stirred for 10 minutes. The organic layer was separated, dried [(NA2SO4),] filtered, and concentrated under reduced pressure. The residue was then recrystallized from [CH2CI2/HEXANES] to provide the product (10 g, 63percent) as a white solid. [(C7H10N202S)] : LC-MS, RT 0.76 min, (M+H) [+] 187.0 ;'H NMR [(CDCI3)] : [6] 2.23 (s, 3H), 3.70 (s, 2H), 3.75 (s, 3H), 4.83-4. 95 (broad s, 2H).
63%	at 100℃; for 1 h;	To a solution of bromide of Example 170 (18 g, 86 mmol) in toluene (100 mL) was added thiourea (10.5 g, 138 mmol). The reaction mixture was heated to 100° C. for 1 hour, cooled to rt, and the solvent removed under reduced pressure. The residue was dissolved with CH₂Cl₂ (100 mL), a saturated solution NaHCO₃ (75 mL) added, and the mixture was vigorously stirred for 10 minutes. The organic layer was separated, dried (Na₂SO₄), filtered, and concentrated under reduced pressure. The residue was then recrystallized from CH₂Cl₂/hexanes to provide the product (10 g, 63percent) as a white solid. (C₇H₁₀N₂O₂S): LC-MS, RT 0.76 min, M+H 187.0; ¹H NMR (CDCl₃): δ 2.23 (s, 3H), 3.70 (s, 2H), 3.75 (s, 3H), 4.83-4.95 (broad s, 2H).
63%	at 100℃; for 1 h;	To a solution of bromide of Example 170 (18 g, 86 mmol) in toluene (100 mL) was added thiourea (10.5 g, 138 mmol). The reaction mixture was heated to 100° C. for 1 hour, cooled to rt, and the solvent removed under reduced pressure. The residue was dissolved with CH₂Cl₂ (100 mL), a saturated solution NaHCO₃ (75 mL) added, and the mixture was vigorously stirred for 10 minutes. The organic layer was separated, dried (Na₂SO₄), filtered, and concentrated under reduced pressure. The residue was then recrystallized from CH₂Cl₂/hexanes to provide the product (10 g, 63percent) as a white solid. (C₇H₁₀N₂O₂S): LC-MS, RT 0.76 min, M+H 187.0; ¹H NMR (CDCl₃): δ 2.23 (s, 3H), 3.70 (s, 2H), 3.75 (s, 3H), 4.83-4.95 (broad s, 2H).

Reference： [1] Patent: WO2004/11446, 2004, A1, . Location in patent: Page 90
[2] Patent: US2018/153859, 2018, A1, . Location in patent: Paragraph 0548; 0549
[3] Patent: US2018/153860, 2018, A1, . Location in patent: Paragraph 0550; 0551

3
[ 30414-53-0 ]
[ 259654-73-4 ]

Reference： [1] Patent: US2018/153860, 2018, A1,
[2] Patent: US2018/153859, 2018, A1,

[ 259654-73-4 ] Synthesis Path-Downstream 1~9

1
[ 17356-08-0 ]
[ 105983-77-5 ]
[ 259654-73-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	In toluene; at 100℃; for 1h;	To a solution of bromide from Step 1 (18 g, 86 [MMOL)] in toluene (100 mL) was added thiourea (10.5 g, 138 [MMOL).] The reaction mixture was heated to [100C] for 1 h, cooled to rt, and the solvent removed under reduced pressure. The residue was dissolved in [CH2CI2] (100 mL), a saturated solution of [NAHC03] (75 mL) was added, and the mixture was vigorously stirred for 10 minutes. The organic layer was separated, dried [(NA2SO4),] filtered, and concentrated under reduced pressure. The residue was then recrystallized from [CH2CI2/HEXANES] to provide the product (10 g, 63%) as a white solid. [(C7H10N202S)] : LC-MS, RT 0.76 min, (M+H) [+] 187.0 ;'H NMR [(CDCI3)] : [6] 2.23 (s, 3H), 3.70 (s, 2H), 3.75 (s, 3H), 4.83-4. 95 (broad s, 2H).
63%	In toluene; at 100℃; for 1h;	To a solution of bromide of Example 170 (18 g, 86 mmol) in toluene (100 mL) was added thiourea (10.5 g, 138 mmol). The reaction mixture was heated to 100 C. for 1 hour, cooled to rt, and the solvent removed under reduced pressure. The residue was dissolved with CH2Cl2 (100 mL), a saturated solution NaHCO3 (75 mL) added, and the mixture was vigorously stirred for 10 minutes. The organic layer was separated, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was then recrystallized from CH2Cl2/hexanes to provide the product (10 g, 63%) as a white solid. (C7H10N2O2S): LC-MS, RT 0.76 min, M+H 187.0; 1H NMR (CDCl3): delta 2.23 (s, 3H), 3.70 (s, 2H), 3.75 (s, 3H), 4.83-4.95 (broad s, 2H).
63%	In toluene; at 100℃; for 1h;	To a solution of bromide of Example 170 (18 g, 86 mmol) in toluene (100 mL) was added thiourea (10.5 g, 138 mmol). The reaction mixture was heated to 100 C. for 1 hour, cooled to rt, and the solvent removed under reduced pressure. The residue was dissolved with CH2Cl2 (100 mL), a saturated solution NaHCO3 (75 mL) added, and the mixture was vigorously stirred for 10 minutes. The organic layer was separated, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was then recrystallized from CH2Cl2/hexanes to provide the product (10 g, 63%) as a white solid. (C7H10N2O2S): LC-MS, RT 0.76 min, M+H 187.0; 1H NMR (CDCl3): delta 2.23 (s, 3H), 3.70 (s, 2H), 3.75 (s, 3H), 4.83-4.95 (broad s, 2H).

Reference： [1]Patent: WO2004/11446,2004,A1 .Location in patent: Page 90
[2]Patent: US2018/153859,2018,A1 .Location in patent: Paragraph 0548; 0549
[3]Patent: US2018/153860,2018,A1 .Location in patent: Paragraph 0550; 0551

2
[ 259654-73-4 ]
[ 24424-99-5 ]
[ 652981-44-7 ]

Yield	Reaction Conditions	Operation in experiment
60%		To a solution of the compound prepared in Step 2 (5.00 g, 26.8 [MMOL)] and DMAP (32 mg, 0.26 [MMOL)] in [CH2C12] (150 mL) was added BOC2O (7.00 g, 32.2 [MMOL).] After 4 h, additional quantities of [BOC20] (7.00 g, 32.2 [MMOL)] and Et3N (7.50 mL, 53.6 [MMOL)] were added. The reaction mixture was stirred at rt for 18 h, then a saturated solution of [NH4CI] (100 mL) was added and the reaction was stirred for 15 minutes. The layers were separated, dried [(NA2SO4),] filtered, and concentrated under reduced pressure. The residue was passed through a short plug of silica gel to yield a mixture of the corresponding mono-and di-carbamate. This mixture was dissolved in [MEOH] (40 mL), and a [1 N SOLUTION] of [NAOH] (20 mL) was added. The solution was stirred for 90 minutes, the methanol removed under reduced pressure and the residue was washed with [ET20] (2 x 10 mL). The aqueous layer was acidified to [PH # 4 ] using 1 N HCI, extracted with CH2CI2 (2 x 50 mL), and the combined organic layers dried [(NA2SO4),] filtered and concentrated under reduced pressure to afford the desired product as a yellow solid (4. [4 G,] 60%). (C11H16N2O4S) : LC-MS, [RT 2.] 39 min, (M+H) [+ 272.] 9 ;'H NMR [(CDCI3)] : [6] 1.51 (s, 9H), 2.32 (s, 3H), [3.] 61 (s, 2H).

Reference： [1]Patent: WO2004/11446,2004,A1 .Location in patent: Page 91

Yield	Reaction Conditions	Operation in experiment
63%		Example 171 Preparation of Methyl (2-amino-5-methyl-1,3-thiazol-4-yl)acetate To a solution of bromide of Example 170 (18 g, 86 mmol) in toluene (100 mL) was added thiourea (10.5 g, 138 mmol). The reaction mixture was heated to 100 C. for 1 hour, cooled to rt, and the solvent removed under reduced pressure. The residue was dissolved with CH2Cl2 (100 mL), a saturated solution NaHCO3 (75 mL) added, and the mixture was vigorously stirred for 10 minutes. The organic layer was separated, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was then recrystallized from CH2Cl2/hexanes to provide the product (10 g, 63%) as a white solid. (C7H10N2O2S): LC-MS, RT 0.76 min, M+H 187.0; 1H NMR (CDCl3): delta 2.23 (s, 3H), 3.70 (s, 2H), 3.75 (s, 3H), 4.83-4.95 (broad s, 2H).

4
[ 30414-53-0 ]
[ 259654-73-4 ]

Reference： [1]Patent: US2018/153860,2018,A1

5
[ 259654-73-4 ]
[ 496062-15-8 ]

Yield	Reaction Conditions	Operation in experiment
40%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at -20 - 15℃; for 2h;	To a solution of CuBr2 (4.03 g, 18.1 mmol) and t-butyl nitrite (2.82 mL, 23.8 mmol) in MeCN (210 mL) was added the compound of Example 170 (2.95 g, 15.9 mmol) at -20 C. The reaction mixture was slowly warmed to 15 C., at which point the evolution of N2 was observed. After stirring for an additional 2 hours at 15 C., the reaction mixture was diluted with Et2O (400 mL) and washed with a 10% solution of HCl (200 mL). The solvent layers were separated, the aqueous re-extracted with Et2O (2*300 mL), and the combined organic layers dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was then purified by silica gel flash chromatography (98:2, hexanes/EtOAc) to afford bromide Example 172 (1.6 g, 40%) as a colorless oil that solidifies upon standing. (C7H8BrNO2S): LC-MS, RT 2.56 min., M+H 250.3; 1H NMR (CDCl3): delta 2.26 (s, 3H), 3.60 (s, 2H), 3.61 (s, 3H).

Reference： [1]Patent: US2018/153859,2018,A1 .Location in patent: Paragraph 0550; 0551

6
[ 259654-73-4 ]
[ 496062-16-9 ]

Reference： [1]Patent: US2018/153859,2018,A1

7
[ 259654-73-4 ]
[ 496063-11-7 ]

Reference： [1]Patent: US2018/153859,2018,A1

8
[ 259654-73-4 ]
((1S)-5-{2-[2-(4-isopropylphenyl)-5-methyl-1,3-thiazol-4-yl]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetic acid [ No CAS ]

Reference： [1]Patent: US2018/153859,2018,A1

9
[ 259654-73-4 ]
[ 496062-17-0 ]

Reference： [1]Patent: US2018/153859,2018,A1

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Isomers

Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • Acyl Group Substitution • Alcohols Convert Acyl Chlorides into Esters • Alcoholysis of Anhydrides • Amides Can Be Converted into Aldehydes • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • Azide Reduction by LiAlH4 • Azide Reduction by LiAlH4 • Basicity of Amines • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Chichibabin Reaction • 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 • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Enamine Formation • Ester Cleavage • Ester Hydrolysis • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Grignard Reagents Transform Esters into Alcohols • Hantzsch Pyridine Synthesis • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hofmann Elimination • Hofmann Rearrangement • Hydride Reductions • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Leuckart-Wallach Reaction • Mannich Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitrosation of Amines • Peptide Bond Formation with DCC • Petasis Reaction • Preparation of Amines • Preparation of LDA • Reactions of Amines • Reactions with Organometallic Reagents • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Reductive Amination • Reductive Amination • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Strecker Synthesis • Synthesis of 2-Amino Nitriles • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • Transesterification • Ugi Reaction

Historical Records

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P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

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. 259654-73-4 ] {[proInfo.proName]}

Quality Control of [ 259654-73-4 ]

Related Doc. of [ 259654-73-4 ]

Product Details of [ 259654-73-4 ]

Calculated chemistry of [ 259654-73-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 259654-73-4 ]

Application In Synthesis of [ 259654-73-4 ]

[ 259654-73-4 ] Synthesis Path-Upstream 1~3

[ 259654-73-4 ] Synthesis Path-Downstream 1~9

Technical Information

Related Functional Groups of [ 259654-73-4 ]

Esters

Amines

Related Parent Nucleus of [ 259654-73-4 ]

Thiazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 259654-73-4 ]

Related Parent Nucleus of
[ 259654-73-4 ]