[ CAS No. 502145-18-8 ] {[proInfo.proName]}

Name: 502145-18-8|2-Amino-4-bromothiazole|95%
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SKU: A266821
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Quality Control of [ 502145-18-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 502145-18-8 ]

Product Details of [ 502145-18-8 ]

CAS No. :	502145-18-8	MDL No. :	MFCD06804547
Formula :	C₃H₃BrN₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QJPQUNWGOHADOB-UHFFFAOYSA-N
M.W :	179.04	Pubchem ID :	428024
Synonyms :

Calculated chemistry of [ 502145-18-8 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	34.22
TPSA :	67.15 Å²

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) :	-6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	1.63
Log Po/w (WLOGP) :	1.5
Log Po/w (MLOGP) :	0.28
Log Po/w (SILICOS-IT) :	2.34
Consensus Log Po/w :	1.44

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.51
Solubility :	0.559 mg/ml ; 0.00312 mol/l
Class :	Soluble
Log S (Ali) :	-2.65
Solubility :	0.398 mg/ml ; 0.00222 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.79
Solubility :	2.93 mg/ml ; 0.0164 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.49

Safety of [ 502145-18-8 ]

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 [ 502145-18-8 ]

* 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 [ 502145-18-8 ]
Downstream synthetic route of [ 502145-18-8 ]

[ 502145-18-8 ] Synthesis Path-Upstream 1~1

1
[ 502145-18-8 ]
[ 1692-25-7 ]
[ 30235-27-9 ]

Yield	Reaction Conditions	Operation in experiment
2.5 mg	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water for 4 h; Inert atmosphere; Reflux	3-pyridyl boronic acid (20mmole), 2-Amino-4-bromo - thiazole (20 mmol) dissolved in Dioxane – water(1:1,70),then added Potassium carbonate (50 mmol) and replaced three times with argongas . the again add Bis (triphenylphosphine) palladium (II) dichloride (1mmol) and the reaction was heatedat reflux for 5h. Cooling, the solvent was distilled off under reducedpressure, the residue was dissolved with methylene chloridethen it was driedover anhydrous sodium sulfate and by column chromatography to give 4-(3-pyridyl) -2-aminothiazole 2.5g.

Reference： [1] Patent: CN103130792, 2016, B, . Location in patent: Paragraph 0733

[ 502145-18-8 ] Synthesis Path-Downstream 1~11

1
[ 13331-23-2 ]
[ 502145-18-8 ]
[ 28989-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; water; N,N-dimethyl-formamide; at 70℃; for 7h;	Example 347 2-(4-Furan-2-yl-thiazol-2-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (Compound 5347) 4-Furan-2-yl-thiazol-2-ylamine <strong>[502145-18-8]4-Bromo-thiazol-2-ylamine</strong> (100 mg, 0.34 mmol) was combined with 57 mg (0.51 mmol) of 2-furan boronic acid. To this mixture was added 5 mL of MeOH, 1 mL of sat. NaHCO3 (aq), and 0.8 mL of DMF. Reaction mixture was degassed and Pd[P(Ph)3]4 (25 mg) was added. Reaction mixture was heated at 70 C. for 7 hours. The reaction mixture was brought to room temperature and filtered. The filtrate was evaporated and purified using reverse phase HPLC.

Reference： [1]Patent: US2007/265265,2007,A1 .Location in patent: Page/Page column 102

2
(R)-piperidine-2-carboxylic acid [ No CAS ]
[ 502145-18-8 ]
[ 1400283-91-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5936 - 5941

3
[ 502145-18-8 ]
[ 52755-02-9 ]
C₆H₈BrN₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 1119 - 1123

4
[ 502145-18-8 ]
[ 108-24-7 ]
N-(4-bromo-1,3-thiazol-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With acetic acid; for 2h;Reflux;	Example 21: Intermediate 23- -(4-bromothiazol-2-yl)acetamide [0266] A solution of <strong>[502145-18-8]4-bromothiazol-2-amine</strong> (0.500 g, 2.81 mmol), acetic anhydride (0.43 mL, 4.50 mmol) and acetic acid (5 mL) was refluxed for 2 h. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 25% ethyl acetate-petroleum ether) to afford N-(4-bromothiazol-2- yl)acetamide (0.300 g, 49%) as a white solid. MS (ESI, pos. ion) m/z 221 , 223 [M+H]+.

Reference： [1]Patent: WO2015/74064,2015,A2 .Location in patent: Paragraph 0266

5
[ 502145-18-8 ]
[ 1692-25-7 ]
[ 30235-27-9 ]

Yield	Reaction Conditions	Operation in experiment
2.5 mg	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; for 4h;Inert atmosphere; Reflux;	3-pyridyl boronic acid (20mmole), 2-Amino-4-bromo - thiazole (20 mmol) dissolved in Dioxane - water(1:1,70),then added Potassium carbonate (50 mmol) and replaced three times with argongas . the again add Bis (triphenylphosphine) palladium (II) dichloride (1mmol) and the reaction was heatedat reflux for 5h. Cooling, the solvent was distilled off under reducedpressure, the residue was dissolved with methylene chloridethen it was driedover anhydrous sodium sulfate and by column chromatography to give 4-(3-pyridyl) -2-aminothiazole 2.5g.

Reference： [1]Patent: CN103130792,2016,B .Location in patent: Paragraph 0733

6
[ 502145-18-8 ]
[ 203866-14-2 ]
tert-butyl (2S,4R)-2-((4-bromothiazol-2-yl)carbamoyl)-4-fluoropyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%		To a stirred solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (250 mg, 1.07 mmole) in 10 mL of CH2Cl2, was added 1-methyl imidazole (0.21 mL, 2.5 equiv.) at 0-5 C. under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0-5 C. and then added methane sulfonyl chloride (0.1 mL, 1.2 equiv) at the same temperature. It was stirred for 1 h at 0-50 C. Then <strong>[502145-18-8]4-bromothiazol-2-amine</strong> (179 mg, 1 equiv) was added, and stirred for 18h at room temperature. Water (10 mL) was added to the reaction mixture, layers were separated and aqueous layer was extracted with DCM (3×10 mL). The combined organic layer was washed with 1N HCl (10 mL), followed by Sat NaHCO3 (10 mL) and then with brine (10 mL). Combined organic layer was dried over Na2SO4, concentrated and 390 mg (97%) of titled compound was obtained.

Reference： [1]Patent: WO2017/35353,2017,A1 .Location in patent: Paragraph 1492

7
[ 502145-18-8 ]
[ 24424-99-5 ]
[ 944804-88-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; In dichloromethane; at 25℃; for 24h;Inert atmosphere;	Di-/er/-butyl dicarbonate (2.43 g, 11.17 mmol) was added to a mixture of 4-bromothiazol-2-amine (2.00 g, 11.17 mmol) and DMAP (136 mg, 1.11 mmol) in CH2CI2 (25 mL) and the mixture was stirred at 25 C for 24 h. The resulting solution was quenched with a saturated aqueous solution of NaHCCE (100 mL) and the mixture was extracted with CH2CI2 (2 x 200 mL). The organic extracts were combined, dried over MgSCL, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (hexane: EtOAc; 1 :0 to 9.5:0.5) to afford the product (2.50 g, 80 %) as a white solid. (0176) NMR (500 MHz, CDCL) (ppm) 8.83 (s, 1H), 6.79 (s, 1H), 1.54 (s, 9H); (0177) 13C NMR (126 MHz, CDCL) (ppm) 160.7, 152.1, 120.6, 110.5, 83.5, 28.3; (0178) HRMS calcd for C8Hi2BrN202S [M+H]+ 280.9777, found 280.9774.

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 15380 - 15405
[2]Patent: WO2019/201867,2019,A1 .Location in patent: Page/Page column 11; 22

8
[ 502145-18-8 ]
2-(4-((3-cyanopyridin-2-yl)oxy)-3-fluorophenyl)acetic acid [ No CAS ]
N-(4-bromothiazol-2-yl)-2-(4-((3-cyanopyridin-2-yl)oxy)-3-fluorophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		To a suspension of intermediate 1 (1.0 g, 3.7 mmol) in DCE (10 mL) was added SOCb (2.7 mL, 37 mmol) and the reaction mixture was heated to 50 C. After 1 h, the solvents were removed under reduced pressure and THF (10 ml), 4-bromothiazol-2- amine (0.70 g, 4.0 mmol), and DIEA (2 mL, 11 mmol) were added. After 24 h, the solvents were removed under reduced pressure and residue was purified via silica gel chromatography to afford (1.1 g, 71 % yield) of N-(4-bromothiazol-2-yl)-2-(4-((3- cyanopyridin-2-yl)oxy)-3-fluorophenyl)acetamide as a brown solid. LCMS(ESI) m/z: 432.7-434.7 (M+H).+ MR (400 MHz, CD3OD) delta 8.32 (dd, 7=5.0, 1.9 Hz, 1H), 8.27 (dd, 7=7.6, 1.9 Hz, 1H), 7.39 - 7.25 (m, 4H), 7.08 (s, 1H), 3.90 (s, 2H).

Reference： [1]Patent: WO2019/14300,2019,A1 .Location in patent: Page/Page column 71

9
[ 4530-20-5 ]
[ 502145-18-8 ]
tert-butyl N-[2-[(4-bromothiazol-2-yl)amino]-2-oxoethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 15℃; for 16h;	To a solution of <strong>[502145-18-8]4-bromothiazol-2-amine</strong> (3.0 g, 16.76 mmol) and 2-(tert-butoxycarbonylamino) acetic acid (4.40 g, 25.13 mmol) in pyridine (30.0 mL) was added EDCI (16.06 g, 83.78 mmol). The mixture was stirred at 15 C for 16 hr. The reaction mixture was then concentrated under reduced pressure. The residue was diluted with 0.5N HCI (1 00.0 mL) and extracted with EtOAc (50 mL *3). The combined organic extracts were washed with NaHC03 (50.0 mL) and brine (50.0 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (S1O2, Petroleum ether/Ethyl acetate=7/1 to 3:1 ) to give intermediate i-74a as a white solid. LCMS (ESI) m/z: [M+Na]+=358.1

Reference： [1]Patent: WO2019/152437,2019,A1 .Location in patent: Page/Page column 154-155

10
[ 502145-18-8 ]
[ 1313399-69-7 ]
7-(2-aminothiazol-4-yl)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99.32%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;	63.1 Step 1: Preparation of 7-(2-aminothiazol-4-yl)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (0832) (Intermediate D) A mixture of 2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinolin- 1(2H)-one [prepared according to the method in Example 7] (200 mg, 696.47 mmol), 4-bromothiazol-2- amine (124.70 mg, 696.47 mmol), K3PO4 (591.35 mg, 2.79 mmol) and [1,1-bis(di-tert- butylphosphino)ferrocene]dichloropalladium(II) (45.39 mg, 69.65 mmol) in dioxane (2 mL) and H2O (0.5 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 100 °C for 2 h under N2 atmosphere. Water (20 mL) was added and the reaction mixture was extracted with EtOAc (50 mL x 2). The combined organic layers were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The crude product was triturated with MeOH (10 mL) at 25 °C for 10 min, then filtered and dried in vacuum to give Intermediate D (180 mg, 691.75 mmol, 99.32% yield) as a white solid. LCMS (ESI) m/z [M+H]+ = 260.1

Reference： [1]Current Patent Assignee: FOGHORN THERAPEUTICS INC - WO2020/160180, 2020, A1 Location in patent: Page/Page column 179

11
[ 313546-19-9 ]
[ 502145-18-8 ]
3-(2-aminothiazol-4-yl)-2-methyl-benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis(tri-t-butylphosphine)palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃;Inert atmosphere;	Bis(tri-te/f-butylphosphine)palladium(0) (29 mg, 0.06 mmol) was added to a degassed solution of 4-bromothiazol-2-amine (100 mg, 0.56 mmol), (3-cyano-2-methyl- phenyl)boronic acid (180 mg, 1.12 mmol) and potassium carbonate (154 mg, 1.12 mmol) in 1 ,4-dioxane (4 ml_) and water (0.8 ml_). The flask was evacuated and backfilled with nitrogen (x 3) and the reaction mixture was stirred at 80 C overnight. The resulting mixture was allowed to cool to room temperature and was partitioned between EtOAc and 70% brine. The organic layer was separated, washed with 70% brine, dried over Na2SC>4 and concentrated in vacuo. Purification by chromatography on silica eluting with a gradient of 2 to 5% MeOH in DCM afforded a brown solid which was triturated with Et2 (1683) 1H NMR (500 MHz, DMSO-d6) d 7.81 (d, J = 7.8 Hz, 1H), 7.74 (d, J = 7.6 Hz, 1H), 7.41 (t, J = 7.7 Hz, 1 H), 7.11 (s, 2H), 6.76 (s, 1H), 2.60 (s, 3H).
	With bis(tri-t-butylphosphine)palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃;Inert atmosphere;	Bis(tri-te/f-butylphosphine)palladium(0) (29 mg, 0.06 mmol) was added to a degassed solution of 4-bromothiazol-2-amine (100 mg, 0.56 mmol), (3-cyano-2-methyl- phenyl)boronic acid (180 mg, 1.12 mmol) and potassium carbonate (154 mg, 1.12 mmol) in 1 ,4-dioxane (4 ml_) and water (0.8 ml_). The flask was evacuated and backfilled with nitrogen (x 3) and the reaction mixture was stirred at 80 C overnight. The resulting mixture was allowed to cool to room temperature and was partitioned between EtOAc and 70% brine. The organic layer was separated, washed with 70% brine, dried over Na2SC>4 and concentrated in vacuo. Purification by chromatography on silica eluting with a gradient of 2 to 5% MeOH in DCM afforded a brown solid which was triturated with Et2 (1683) 1H NMR (500 MHz, DMSO-d6) d 7.81 (d, J = 7.8 Hz, 1H), 7.74 (d, J = 7.6 Hz, 1H), 7.41 (t, J = 7.7 Hz, 1 H), 7.11 (s, 2H), 6.76 (s, 1H), 2.60 (s, 3H).

Reference： [1]Patent: WO2022/23772,2022,A1 .Location in patent: Paragraph 00394
[2]Patent: WO2022/23772,2022,A1 .Location in patent: Paragraph 00394

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
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Prevention
Code	Phrase
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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

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

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. 502145-18-8 ] {[proInfo.proName]}

Quality Control of [ 502145-18-8 ]

Related Doc. of [ 502145-18-8 ]

Product Details of [ 502145-18-8 ]

Calculated chemistry of [ 502145-18-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 502145-18-8 ]

Application In Synthesis of [ 502145-18-8 ]

[ 502145-18-8 ] Synthesis Path-Upstream 1~1

[ 502145-18-8 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 502145-18-8 ]

Bromides

Amines

Related Parent Nucleus of [ 502145-18-8 ]

Thiazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 502145-18-8 ]

Related Parent Nucleus of
[ 502145-18-8 ]