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[ CAS No. 933728-73-5 ]

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Chemical Structure| 933728-73-5
Chemical Structure| 933728-73-5
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Product Details of [ 933728-73-5 ]

CAS No. :933728-73-5 MDL No. :MFCD09879069
Formula : C7H9BrN2OS Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :249.13 g/mol Pubchem ID :-
Synonyms :

Safety of [ 933728-73-5 ]

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

Application In Synthesis of [ 933728-73-5 ]

  • 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 ]
YieldReaction ConditionsOperation 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.
  • 2
  • [ 933728-73-5 ]
  • [ 1175273-39-8 ]
  • [ 1175273-48-9 ]
YieldReaction ConditionsOperation 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).
  • 3
  • [ 933728-73-5 ]
  • [ 1175274-83-5 ]
  • [ 1175275-19-0 ]
YieldReaction ConditionsOperation 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).
  • 5
  • [ 876322-58-6 ]
  • [ 933728-73-5 ]
  • N-(4-methyl-3-(2-morpholinothiazol-5-yl)phenyl)-3-(trifluoromethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 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 ]
YieldReaction ConditionsOperation 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%).
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation 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.
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