[ CAS No. 28599-52-2 ]

Name: 28599-52-2|5-Bromo-2,4-dimethyl-1,3-thiazole|95%
Brand: Ambeed
SKU: A410413
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3d Animation Molecule Structure of 28599-52-2

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Quality Control of [ 28599-52-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 28599-52-2 ]

SDS Specification

Alternatived Products of [ 28599-52-2 ]

Product Details of [ 28599-52-2 ]

CAS No. :	28599-52-2	MDL No. :	MFCD03086099
Formula :	C₅H₆BrNS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BSFCVAYFJQLZEU-UHFFFAOYSA-N
M.W :	192.08 g/mol	Pubchem ID :	298628
Synonyms :

Calculated chemistry of [ 28599-52-2 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.4
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.75
TPSA :	41.13 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.14
Log Po/w (XLOGP3) :	2.78
Log Po/w (WLOGP) :	2.52
Log Po/w (MLOGP) :	1.29
Log Po/w (SILICOS-IT) :	3.64
Consensus Log Po/w :	2.47

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.24
Solubility :	0.109 mg/ml ; 0.000569 mol/l
Class :	Soluble
Log S (Ali) :	-3.3
Solubility :	0.0963 mg/ml ; 0.000501 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.92
Solubility :	0.229 mg/ml ; 0.00119 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.39

Safety of [ 28599-52-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 28599-52-2 ]

* 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 [ 28599-52-2 ]
Downstream synthetic route of [ 28599-52-2 ]

[ 28599-52-2 ] Synthesis Path-Upstream 1~3

1
[ 28599-52-2 ]
[ 74-88-4 ]
[ 13623-11-5 ]

Reference： [1] Zhurnal Obshchei Khimii, 1956, vol. 26, p. 66; engl. Ausg. S. 65

2
[ 28599-52-2 ]
[ 50382-32-6 ]

Reference： [1] Zhurnal Obshchei Khimii, 1956, vol. 26, p. 66; engl. Ausg. S. 65

3
[ 28599-52-2 ]
[ 53137-27-2 ]

Reference： [1] Zhurnal Obshchei Khimii, 1956, vol. 26, p. 66; engl. Ausg. S. 65

[ 28599-52-2 ] Synthesis Path-Downstream 1~7

1
[ 28599-52-2 ]
[ 74-88-4 ]
[ 13623-11-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1956,vol. 26,p. 66; engl. Ausg. S. 65

2
[ 28599-52-2 ]
[ 50382-32-6 ]

Reference： [1]Zhurnal Obshchei Khimii,1956,vol. 26,p. 66; engl. Ausg. S. 65

3
[ 28599-52-2 ]
[ 53137-27-2 ]

Reference： [1]Zhurnal Obshchei Khimii,1956,vol. 26,p. 66; engl. Ausg. S. 65

4
[ 28599-52-2 ]
[ 89641-18-9 ]
C₁₁H₁₃N₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 4-bromo-2,5-dimethyl-1 ,3-thiazole (commercially available from Apollo Scientific Ltd, 410 mg, 2.135 mmol) in 1 ,2-Dimethoxyethane (DME) (6.5 mL), Tetrakis(triphenylphosphine)palladium (123 mg, 0.107 mmol) was added and the mixture was stirred at rt for 30 minutes. Then <strong>[89641-18-9][2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid</strong> ( <n="62"/>commercially available from Aldrich, 916 mg, 4.48 mmol) and 1 M Sodium bicarbonate aqueous solution (5.83 ml_, 5.83 mmol) were added. The reaction mixture was then stirred at 9O0C for 2.5h and left stirring at rt overnight. The day after the mixture was diluted with DCM and washed with water. Organic layer was dried and concentrated under vacuum . Crude product was first purified by flash chromatography (eluent: Cy/AcOEt 65:35) and further purified by SCX cartridge affording 5-(2,5-dimethyl-1 ,3- thiazol-4-yl)-2,4-bis(methyloxy)pyrimidine with minor unknown impurities that was used in the next step without further purification.

Reference： [1]Patent: WO2009/43883,2009,A1 .Location in patent: Page/Page column 60-61

5
[ 28599-52-2 ]
[ 22536-67-0 ]
[ 930580-28-2 ]

Yield	Reaction Conditions	Operation in experiment
32%		Step 2.To a solution of 73 (5 g, 26 mmol) in THF (50 mL) was added n-BuLi (11 mL, 27.5 mmol) at - 78 C and stirred at -78 C for 30 min. Then 74 in THF (15 mL) was added at -78 C, and stirred at rt overnight. H20 (544 mg, 30 mmol) in THF (5 mL) was added at 0 C, and stirred at rt for 1 h, then DDQ (5.9 g, 26 mmol) in THF (30 mL) was added and stirred at rt overnight. The mixture was partitioned between H20 and EA and the organic layer was dried and concentrated. The residue was purified by column (PE:EA=10: 1) to afford 75 (2.2 g, 32% yield).

Reference： [1]Patent: WO2015/58163,2015,A2 .Location in patent: Paragraph 239

6
[ 28599-52-2 ]
[ 857003-04-4 ]
[ 139022-25-6 ]
[ 1362160-35-7 ]

Reference： [1]Patent: WO2012/31197,2012,A1 .Location in patent: Page/Page column 408-409

7
[ 28599-52-2 ]
[ 61676-62-8 ]
[ 859833-13-9 ]

Yield	Reaction Conditions	Operation in experiment
26%	Stage #1: 5-bromo-2,4-dimethyl-1,3-thiazole With magnesium In tetrahydrofuran; ethylene dibromide at 75℃; for 5h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; ethylene dibromide at 0 - 20℃; for 20h;	1 Production of 2,4 -Dim at hyl-5-(4, 45, 5-tetramethyl-1, 3, 2-dioxaboroIan-2-yfltliazo1e (9) A solution of 5-bromo-2,4-dimethylthiazole (8) (5.00 g. 26.0 mmo) and 1 .2- dibromoethane (0.24 91 1.3 mmol) in THF (20 mL) was added dropwise to a flask containing magnesium turnings (0.65 g, 26.8 rnmol) over a one hour period. The reaction mixture was heated to 75 CC for 4 hours, cooled to ambient temperature then transferred to a dropping funnel 4a a cannula on a second reaction flask. The Grignard reagent was then added dropwise to a solution of sopropypinacolborate (5.30 mL, 26.00 mnmol) in THF (10 mL.) at 0 t. After addition was complete, the reaction mixture was warmed up to ambient temperature and was stirred for 20 hours. The reaction was cooled to -10 CC, and then slowly acetic acid (1.03 mL. 25.50 mmol) was added so that the reaction mixture was at pH 7. Solvent was removed by rotary evaporation then ethyl acetate was added and also removed by rotary evaporation. The crude oil was preabsorbed onto Celite then chromatographed (DCVC) eluting with a gradient of ethyl acetate th heptane (0 - 30% ethyl acetate). Fractions containing the desired material were combined and concentrated to give 2.4-dimethyl-5-(44.5.5-tetramethyl-1 .3,2- dioxaborolan-2-thiaz.ole (9) as a pale yellow oil which solidified (1.65 9, 26%). NMR (400 MHz, DMSO-&)6 2.63 (s. 3H), 2.53 (s. 3H), 1.2 s, 12H). C NMR (50 MHz, DMSO-d10o 170.4.163.21 84.1, 24.9. 19.1.17.6 (one signal not observed). ElMS: rn1z Found: M’ 239.1143, CllHlFNO211B%requires239.i 146. ElMS: rn/z239(M, 66%), 224 (45), 182 7). 139 t,53L 71(100).
	With n-butyllithium In tetrahydrofuran at -78 - 30℃; for 2.5h;	12.2 Step 2: synthesis of compound WX022-3 (0142) WX022-2 (5 g, 26.03 mmol, 1 eq.; crude) and WX016-3 (14.53 g, 78.09 mmol, 15.93 mL, 3 eq.) were dissolved in tetrahydrofuran (150 mL), and n-butyllithium (2.5 M, 31.24 mL, 3 eq.) was added at -78 °C. The mixture was stirred at -78 °C for 1 h and then at 30 °C for 1.5 h. The reaction system was added with methanol (about 100 mL) to quench the reaction, and concentrated to give crude WX022-3, which was used directly in the next step.

Reference： [1]Current Patent Assignee: VECTUS BIOSYSTEMS LIMITED; ACCUGEN - WO2016/145478, 2016, A1 Location in patent: Paragraph 0099
[2]Current Patent Assignee: WUXI APPTEC CO., LTD. - EP3828184, 2021, A1 Location in patent: Paragraph 0139-0140; 0142

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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. 28599-52-2 ]

Quality Control of [ 28599-52-2 ]

Related Doc. of [ 28599-52-2 ]

Product Details of [ 28599-52-2 ]

Calculated chemistry of [ 28599-52-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 28599-52-2 ]

Application In Synthesis of [ 28599-52-2 ]

[ 28599-52-2 ] Synthesis Path-Upstream 1~3

[ 28599-52-2 ] Synthesis Path-Downstream 1~7

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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