[ CAS No. 933728-73-5 ] {[proInfo.proName]}

Name: 933728-73-5|4-(5-Bromothiazol-2-yl)morpholine|98%
Brand: Ambeed
SKU: A423890
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Quality Control of [ 933728-73-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 933728-73-5 ]

SDS Specification

Alternatived Products of [ 933728-73-5 ]

Product Details of [ 933728-73-5 ]

CAS No. :	933728-73-5	MDL No. :	MFCD09879069
Formula :	C₇H₉BrN₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UJOKEKHNLUXDEY-UHFFFAOYSA-N
M.W :	249.13	Pubchem ID :	45787551
Synonyms :

Calculated chemistry of [ 933728-73-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.57
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.54
TPSA :	53.6 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) :	-6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.23
Log Po/w (XLOGP3) :	2.06
Log Po/w (WLOGP) :	1.36
Log Po/w (MLOGP) :	0.82
Log Po/w (SILICOS-IT) :	2.86
Consensus Log Po/w :	1.87

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.92
Solubility :	0.296 mg/ml ; 0.00119 mol/l
Class :	Soluble
Log S (Ali) :	-2.81
Solubility :	0.382 mg/ml ; 0.00153 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.34
Solubility :	1.14 mg/ml ; 0.00459 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.77

Safety of [ 933728-73-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P310	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 933728-73-5 ]

* 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 [ 933728-73-5 ]

[ 933728-73-5 ] Synthesis Path-Downstream 1~8

1
[ 110-91-8 ]
[ 4175-78-4 ]
[ 933728-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethanol; at 150℃; for 2h;	Step 1: A solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (1.0 equiv.), morpholine (1.5 equiv.) and triethylamine (4 equiv.) were heated to 150 C. for 2 h in the microwave. After concentration, the mixture was partitioned between water and EtOAc. The organic phase was washed with brine and dried over sodium sulfate. The solution was concentrated and dried under vacuo to give crude N-(4-methyl-3-(2-morpholinothiazol-5-yl)phenyl)-3-(trifluoromethyl)benzamide and was used in the next step without further purification. LCMS (m/z) (M+H)=448.2, Rt=0.83 min.

Reference： [1]Patent: US2014/275003,2014,A1 .Location in patent: Paragraph 0708; 0709

2
[ 933728-73-5 ]
[ 1175273-39-8 ]
[ 1175273-48-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-(5-bromothiazol-2-yl)morpholine; 3-(5-chloro-8-fluoroisoquinolin-3-yl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine With potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 0.75h; Microwave irradiation; Stage #2: With hydrogenchloride In diethyl ether; dichloromethane	61 Example 61; 3-(5-Chloro-8-fluoroisoquinolin-3-yl)-5-(2-morpholin-4-ylthiazol-5-yl)-pyridin-2-ylamine; A solution of 4-(5-bromo-thiazol-2-yl)-morpholine (52.4 mg, 0.210 mmol), 3-(5-chloro-8-fluoroisoquinolin-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-ylamine (BB5) (70 mg, 0.18 mmol), potassium carbonate (77.5 mg, 0.560 mmol), and Pd(PPh3)4 (0.01 g, 0.01 mmol) in previously degassed DME/water (4:1) (1.95 mL) was placed in a microwave tube and evacuated and charged with N2 (2×). The reaction mixture was heated in the microwave reactor to 100° C. for 45 min. The reaction mixture was partitioned between CHCl3 and H2O, and the layers were separated. The aqueous layer was re-extracted with CHCl3 (3 ×) and the combined organic fractions were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by chromatography on silica gel [eluting with 1.5% MeOH in CHCl3] resulting in a yellow solid slightly contaminated with triphenylphosphine oxide. Therefore, this material was dissolved in MeOH/THF and passed through a prewashed 5 g SCX column. The column was washed with 2 volumes of MeOH and 2 volumes of THF then was washed with 1M NH4OH in MeOH upon which the product was released from the resin. The filtrate was concentrated in vacuo, and the resulting material was chromatographed on silica gel [eluting with 0.5% MeOH in CHCl3] resulting in the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=3.37-3.49 (m, 4H), 3.68-3.81 (m, 4H), 7.05 (s, 2H), 7.51-7.62 (m, 2H), 8.03 (dd, J=8.4, 4.8 Hz, 1H), 8.07 (d, J=2.2 Hz, 1H), 8.23 (d, J=2.2 Hz, 1H), 8.36 (s, 1H), 9.64 (s, 1H). MS (ES+): m/z=442.06/444.03 (76/24) [MH+]. HPLC: tR=3.06 min (ZQ2, polar-5 min).

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2009/197862, 2009, A1 Location in patent: Page/Page column 44

3
[ 933728-73-5 ]
[ 1175274-83-5 ]
[ 1175275-19-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 0.75h; Microwave irradiation;	120 Example 120; 3-Benzothiazol-2-yl-5-(2-morpholin-4-ylthiazol-5-yl)-pyridin-2-ylamine; A solution of 4-(5-bromothiazol-2-yl)-morpholine (0.0600 g, 0.241 mmol), 3-benzothiazol-2-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-ylamine (BB8) (0.110 g, 0.313 mmol), potassium carbonate (0.106 g, 0.771 mmol), and Pd(PPh3)4 (0.02 g, 0.02 mmol) in previously degassed DME/Water (4:1) (2.7 mL) was placed in a microwave tube and evacuated and charged with N2 (2×). The reaction mixture was heated in the microwave reactor at 100° C. for 45 min. The reaction mixture was partitioned between CHCl3 and H2O and the layers were separated. The aqueous layer was re-extracted with CHCl3 (3×), and the combined organic extracts were washed with brine (1×), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was submitted for MDP for purification. The pure fractions were combined and the organic was concentrated in vacuo then diluted with CHCl3 and neutralized with sat. NaHCO3. The layers were separated, and the aqueous layer was re-extracted with CHCl3 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo, giving the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=3.44 (d, J=5.1 Hz, 4H), 3.73 (d, J=5.1 Hz, 4H), 7.49 (t, J=7.7 Hz, 1H), 7.57 (t, J=7.7 Hz, 1H), 7.61 (s, 1H), 8.00 (d, J=2.2 Hz, 1H), 8.03 (br. s., 2H), 8.10 (d, J=7.7 Hz, 1H), 8.15 (d, J=7.3 Hz, 1H), 8.36 (d, J=2.2 Hz, 1H). MS (ES+): m/z=396.07 (100) [MH']. HPLC: tR=3.57 min (ZQ2, polar-5 min).

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2009/197862, 2009, A1 Location in patent: Page/Page column 59

4
[ 3034-55-7 ]
[ 5765-65-1 ]
[ 933728-73-5 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 4667 - 4670
Angew. Chem.,2014,vol. 126,p. 4755 - 4758,4

5
[ 876322-58-6 ]
[ 933728-73-5 ]
N-(4-methyl-3-(2-morpholinothiazol-5-yl)phenyl)-3-(trifluoromethyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane at 108℃; for 0.216667h; Microwave irradiation;	198.2 N-(4-methyl-3-(2-morpholinothiazol-5-yl)phenyl)-3-(trifluoromethyl)benzamide Step 2: A mixture of 4-(5-bromothiazol-2-yl)morpholine (1.0 equiv.), N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(trifluoromethyl)benzamide (1.2 equiv.), sodium carbonate (2 M, 8 equiv.) and PdCl2(dppf) (0.5 equiv.) in DME (0.1 M) were heated to 108° C. for 13 min in the microwave. After removing the DME soluble portion and concentrating, the resulting solid was partitioned between EtOAc and water. The organic phase was washed with brine and then dried over magnesium sulfate. After concentration, the crude material was purified via preparative reverse phase HPLC. Upon lyophilization of the pure fractions, N-(4-methyl-3-(2-morpholinothiazol-5-yl)phenyl)-3-(trifluoromethyl)benzamide was isolated as the TFA salt in 15% yield. 1H NMR (400 MHz, ) δ ppm 2.36 (s, 3H) 3.40-3.43 (m, 4H) 3.70-3.74 (m, 4H) 7.22-7.33 (m, 2H) 7.63 (dd, J=8.22, 1.96 Hz, 1H) 7.72-7.84 (m, 2H) 7.95 (d, J=7.43 Hz, 1H) 8.19-8.33 (m, 2H) 10.45 (s, 1H). LCMS (m/z) (M+H)=448.2, Rt=0.83 min.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Barsanti, Paul A.; Burger, Matthew; Lou, Yan; Nishiguchi, Gisele; Polyakov, Valery; Ramurthy, Savithri; Rico, Alice; Setti, Lina; Smith, Aaron; Taft, Benjamin; Tanner, Huw; DiPesa, Alan; Yusuff, Naeem - US2014/275003, 2014, A1 Location in patent: Paragraph 0708; 0710

6
[ 933728-73-5 ]
(R)-4-((R)-1-((3-cyclopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one [ No CAS ]
(R)-4-((R)-1-((3-cyclopropyl-6-(2-morpholinothiazol-5-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15.5%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 2h; Microwave irradiation; Inert atmosphere; Sealed tube;	Preparation of (R)-4-((R)-1-((3-cyclopropyl-6-(2-morpholinothiazol-5-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one To a microwave tube equipped with a stirring bar, (R)-4-((R)-1-((3-cyclopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (165.5 mg, 0.401 mmol), 4-(5-bromothiazol-2-yl)morpholine (120 mg, 0.482 mmol), 1,2-dimethoxyethane (2 mL), 1 N Na2CO3 aqueous solution (1.20 mL, 1.20 mmol) were added, the mixture was bubbled N2 for 5 minutes before Pd(PPh3)4 (23.2 mg, 0.02 mmol) was added. The tube was sealed and heated in an oil bath at 100° C. for 2 hrs. DCM (200 mL) was added and the resulting mixture was washed with saturated NaHCO3 aqueous solution (20 mL×4), brine (20 mL×1), dried over anhydrous Na2SO4, filtered, removed solvents in vacuo. The resulting residue was passed a ISCO silica gel column (MeOH: DCM=5:95) to give brown solids, 28.3 mg (yield 15.5%).

Reference： [1]Current Patent Assignee: KRONOS BIO INC - KR2016/37198, 2016, A Location in patent: Paragraph 2052-2054

Yield	Reaction Conditions	Operation in experiment
300 mg	With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 80℃; for 8h;	5.5a Step 1b: Preparation of 1-(5-bromothiazol-2-yl)piperidin-4-ol General procedure: To 2,5-dibromothiazole (500mg, 2.06mmol) Add piperidin-4-ol (250mg, 2.47mmol) and N,N-diisopropylethylamine (372mg, 2.88mmol) to the solution of 1,4-dioxane (30mL).The mixture was stirred at 80°C for 8 hours.The mixture was diluted with ethyl acetate (100 mL),Then washed with water (100mL) and saturated brine (100mL),Then dry with anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain a crude product.The crude product was purified by column chromatography to obtain 1-(5-bromothiazol-2-yl)piperidin-4-ol (310 mg) as a brown solid.

8
[ 933728-73-5 ]
3-(2-chloro-3-fluorophenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine [ No CAS ]
4-(5-(3-(2-chloro-3-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl)thiazol-2-yl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.8%	With C₄₇H₆₃NO₃PPdS; potassium carbonate In 1,2-dimethoxyethane; water at 110℃; for 16h;	1.11 (11) Add 3-(2-chloro-3-fluorophenyl)-5-(4,4,5,5-tetramethyl-1,2,3-dioxaborane-2-yl)pyrazolo[1,5-a]pyridine (252mg) was dissolved in DME/water (2:1, 6mL). Weigh 4-(5-bromothiazol-2-yl)morpholine (153 mg, 0.616 mmol) and potassium carbonate (170 mg, 1.23 mmol) into the reaction flask. XPhos Pd G4 (15mg, 0.031mmol) was quickly added and replaced with argon three times. The system was heated to 110 °C and reacted for 16 hours. After cooling down to room temperature, filter on a celite pad and column chromatography to obtain a yellow solid (20mg, 7.8% yield). The yellow solid is 4-(5-(3-(2-chloro-3-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl)thiazol-2-yl)morpholine.

Reference： [1]Current Patent Assignee: NANJING GURUI BIOLOGICAL TECH - CN113336751, 2021, A Location in patent: Paragraph 0041; 0067-0069

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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. 933728-73-5 ] {[proInfo.proName]}

Quality Control of [ 933728-73-5 ]

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[ 933728-73-5 ] Synthesis Path-Downstream 1~8

Related Functional Groups of [ 933728-73-5 ]

Bromides

Related Parent Nucleus of [ 933728-73-5 ]

Morpholines

Thiazoles

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[ 933728-73-5 ]

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[ 933728-73-5 ]