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CAS No. : | 1257705-09-1 | MDL No. : | MFCD31382011 |
Formula : | C17H19N5O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BYWJAVQGRJEEHH-UHFFFAOYSA-N |
M.W : | 357.43 | Pubchem ID : | 67479440 |
Synonyms : |
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Chemical Name : | 4-(4-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzyl)thiomorpholine 1,1-dioxide |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; N,N-dimethyl-formamide; at 80℃; for 18h;Inert atmosphere; Sealed tube;Product distribution / selectivity; | 5- {4-[(l , 1 -dioxidothiomorpholin-4-yl)methyl]phenyl} [ 1 ,2,4]triazolo[ 1 ,5-a]pyridin- 2-amine was prepared from 5-bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (368 mg, 1.73 mmol) and 4-[(4-boronophenyl)methyl]-thiomorpholine 1,1-dioxide (0.512 mg, 1.90 mmol), in a manner analogous to Step 73c. The residue was purified on a 12 g Isco silica gel column using a gradient of 0-15% methanol in dichloromethane as an eluent. 5- {4- [(1,1 -dioxidothiomorpholin-4-yl)methyl]phenyl} [ 1 ,2,4]triazolo[ 1 ,5-a]pyridin-2-amine (490 mg, 79 %) was isolated as a beige foam. 1H NMR (400 MHz, (D3C)2SO, delta, ppm): 7.93 (d, J = 8.5 Hz, 2H), 7.50 (m, 3H), 7.37 (d, J = 7.8 Hz, IH), 7.07 (d, J= 7.8 Hz, IH), 6.02 (s, 2H), 3.78 (s, 2H), 3.15 (s, 4H), 2.91 (s, 4H). MS = 358 (MH)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 16h;Inert atmosphere; | 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (30.00 g, 0.14 mol) was added to a 1L three-necked bottle,To which 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane-2-yl)-benzyl]-1,1-diyl is added successively oxygen-1-Thiomorpholine (58.50 g, 0.15 mol),Dioxane (400 mL),Potassium carbonate (58.60g, 0.42mol),Water (100mL),Pd(dppf)Cl2 (5.78 g, 0.007 mol).Under argon protection,The mixture was warmed to 90 C and the reaction was stirred for 16 hours. After the reaction was completed, the mixture was cooled to room temperature, 400 mL of dichloromethane was added, and then washed twice with 800 mL of water each time. The organic layer was concentrated to dryness and the residue was purified by column chromatography (eluent: dichloromethane:methanol= 100:1), the title product was obtained as a pale yellow solid 27.2 g, yield 54%. |
54% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 16h;Inert atmosphere; | 3-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (purchased from Mesh Mall) 30.00 g (0.14 mol) was added to a 1L three-necked bottle,4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzyl) is added thereto in this orderThiomorpholine 1,1-dioxide 58.50 g (0.15 mol), dioxane 400 ml, potassium carbonate 58.60 g (0.42 mol), water 100 ml, Pd(dppf)Cl2 5.78 g (0.007 mol).Under argon protection, the mixture was warmed to 90 C and the reaction was stirred for 16 h.After the reaction is completed, cool to room temperature, add 400 ml of dichloromethane, then wash twice with water, 800 ml each time, and concentrate the organic layer to dryness.The residue was purified by column chromatography (eluent: dichloromethane:methanol = 100:1) to give the title product as a pale yellow solid, 27.2 g, 54% yield, purity 96%. |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In water; at 90℃; for 16h;Inert atmosphere; Heating; | 4-[ 4-( 4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzyl]-thiomorpholine-1, 1-dioxide(1.1eq.) was added to a solution of 5-bromo-[1,2,4]triazolo[1,5-a]pyrid in-2-ylamine (4:1). K2C03 (2eq.) and PdCbdppf (0.03 eq.) were added to the solution. The resulting mixture was then heated in anoil bath at 90C for 16h under N 2. Water was added and the solution was extracted with ethyl acetate.The organic layers were dried over anhydrous MgS04 and evaporated in vacuo. The final compoundwas obtained after purification by flash chromatography.[00162] 1H (400 MHz, CDCh) 8 7.94-7.92 (d, 2H), 7.52-7.48 (m, 3H), 7.37-7.34 (m, 1H), 7.02-7.00(m, 1H), 6.00 (d, 2H), 3.76 (d, 2H), 3.15-3.13 (m, 4H), 2.93-2.91 (m, 4H).[00163] m/z 358.2 (M+H+, 100%). |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 85 - 90℃; | 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)benzyl)thiomorpholine 1,1-dioxide (2 eq) of Formula (III) was added to a solution of <strong>[1010120-55-4]5-Bromo-[1,2,4]Triazolo[1,5-a]pyridine-2-ylamine</strong> of Formula (II) in 1,4-dioxane/ water (5:1). Cesium carbonate Cs2CO3 (2 eq.) and PdCl2dppf (0.05%) was added to above solution. The resulting mixture was then heated in at 85-90 C. Water was added and to obtain 4-(4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzyl)thiomorpholine1,1-dioxide compound of Formula (IV). |