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[ CAS No. 959755-46-5 ] {[proInfo.proName]}

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Product Details of [ 959755-46-5 ]

CAS No. :959755-46-5 MDL No. :MFCD11040378
Formula : C5H2Br2N4 Boiling Point : -
Linear Structure Formula :- InChI Key :IDWOTLNDEITXRA-UHFFFAOYSA-N
M.W : 277.90 Pubchem ID :49758022
Synonyms :

Safety of [ 959755-46-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 959755-46-5 ]

* 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 [ 959755-46-5 ]

[ 959755-46-5 ] Synthesis Path-Downstream   1~38

  • 1
  • [ 959755-44-3 ]
  • [ 959755-46-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(3,6-dibromo-pyrazin-2-yl)-N'-hydroxyformamidine With PPA at 50 - 70℃; for 2.75h; Stage #2: With sodium hydrogencarbonate In water at 20℃; 3 N-(3,6-dibromo-pyrazin-2-yl)-jV-hydroxyformamidine (17.4 mg, 58.80 mmol) is treated with polyphosphoric acid (150 g) for one hour at 5O0C and then for 1.75 hours at 7O0C. After cooling to room temperature, water is added to the reaction mixture. The resultant suspension is brought to pH 8 by careful addition of solid NaHCθ3 in small portions. The precipitate formed is collected by filtration, washed once with IN NaOH, three times with water and dried in vacuo. The residue is partitioned between ethyl acetate and IN NaOH and the organic phase is washed one more time with IN NaOH and once with brine. The organic phase is dried over MgSOzi, filtered and evaporated to give the title compound (10.15 g) as a white solid. 1H-NMR (400MHz, Cl6-DMSO) δ(ppm) 8.43 (s, IH), 8.92 (s, IH). LCMS: Rt 2.73 min (94.2 %), m/z (APCI) 277 (M+H)+.
  • 2
  • [ 2524-67-6 ]
  • [ 959755-46-5 ]
  • [ 959755-48-7 ]
YieldReaction ConditionsOperation in experiment
94% With N-ethyl-N,N-diisopropylamine In isopropyl alcohol for 4.5h; Heating / reflux; 4 A mixture of 5,8-dibromo-[l,2,4]triazolo[l,5-a]pyrazine (123 mg, 443 μmol), 4-(4- morpholino)aniline (118 mg. 0.664mmol) and N-ethyldiisopropylamine (116 mL, 0.664mmol) is heated at reflux in 2-propanol (3 mL) for 4.5 hours. The reaction mixture is evaporated to dryness and the residue partitioned between dichloromethane and citric acid (10 %). The organic phase is washed once with water and brine, dried over MgSOzi, filtered and evaporated to furnish the title compound (156 mg, 94 %) as a yellow solid. 1H-NMR (400MHz, Cl6-DMSO) δ(ppm) 3.11 (m, 4H), 3.78 (m, 4H), 6.97 (d, 2H), 7.82 (d, 2H), 7.87 (s, IH), 8.71 (s, IH), 9.93 (br s, IH). LCMS, Rt 3.32 min (96.8 %) m/z (APCI) 375 (M+H)+.
  • 3
  • [ 959755-46-5 ]
  • [ 16153-81-4 ]
  • [ 959755-52-3 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 80℃; for 8h; 1 A mixture of 5,8-dibromo-[l,2,4]triazolo[l,5-a]pyrazine (2 g, 7.20 mmol), 4-(4- methyl-piperazin-l-yl)-phenylamine (1.65 g, 8.64 mmol) and N-ethyldiisopropyl-amine (1.5 mL, 8.64 mmol) is heated at 8O0C in 2-propanol (50 mL) for 8 hours. The reaction mixture is evaporated to dryness and the residue partitioned between dichloromethane and water. The aqueous phase is extracted twice with dichloromethane. The organic layers are washed with brine, dried over MgSOzi, filtered and evaporated to furnish the title compound (1.41 g) as a grey solid. 1H-NMR (400MHz, c^- DMSO) δ(ppm) 2.27 (3H, s), 2.54 (4H, m), 3.14 (4H, m), 6.97 (2H, d), 7.80 (2H, d), 7.87 (IH, s), 8.72 (IH, s), 9.92 (IH, br s). LCMS: Rt 2.07 min (77.4 %), m/z (APCI) 388 (M+H)+.
  • 4
  • [ 957346-19-9 ]
  • [ 959755-46-5 ]
  • [ 959755-61-4 ]
YieldReaction ConditionsOperation in experiment
46% With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 90℃; for 8h; 4 A mixture of 5,8-dibromo-[l,2,4]triazolo[l,5-a]pyrazine (0.391g, 1.41mmol), 3-(tert- butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenylamine (0.5g, 1.55mmol) and N- ethyldiisopropyl-amine (0.27mL, 1.55mmol) is heated at 9O0C in 2-propanol (1OmL) for 8 hours. The reaction mixture is evaporated to dryness and the residue partitioned between dichloromethane and water. The aqueous phase is extracted twice with dichloromethane. The organic layers are combined, washed with brine, dried over MgSOzi, filtrated and concentrated in vacuo to afford the title compound (335mg, 46%).
  • 5
  • [ 837421-92-8 ]
  • [ 959755-46-5 ]
  • [ 959756-11-7 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol for 48h; Heating / reflux; 3 N,N-Diisopropylethylamine (200 μL, 1.2 mmol) is added to a mixture of 4-(l- isopropylpiperidin-4-yl)phenylamine (220 mg, 1.0 mmol) and 5,8-dibromo-[l,2,4]triazolo[l,5- a]pyrazine (280 mg, 1.0 mmol) in 1PrOH (5 mL) and heated at reflux for 48 h. The mixture is cooled and the solvent evaporated under reduced pressure to afford an orange-brown solid. This is partitioned between DCM (50 mL) and water (20 mL) and the layers are separated. The organic phase is washed with citric acid (10% aq., 3 x 25 mL). The combined washings are extracted with DCM (25 mL) and then made basic by addition of NaHCθ3 (s). The mixture is extracted with DCM (3 x 25 mL) and the combined extracts dried over MgSθ4 and evaporated. The crude product was purified by chromatography on silica gel, eluting with 5% - 10% MeOH in DCM to afford the desired compound, contaminated with the starting aniline. This was recrystallised from MeOH to afford the pure title compound (110 mg).
  • 6
  • [ 959756-39-9 ]
  • [ 959755-46-5 ]
  • [ 959756-40-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide; 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine With hydrogen bromide In water; isopropyl alcohol for 24h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water; isopropyl alcohol 3 5,8-Dibromo-[l,2,4]triazolo[l,5-a]pyrazine (285 mg, 1.03 mmol) and 4-amino-2- methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide (280 mg, 1.03 mmol) are stirred in 1PrOH (5 mL) and HBr (48% aq., 380 μL) is added. The mixture is heated at reflux for 24 hours. The cooled suspension is poured into NaHCθ3 (sat. aq., 25 mL) and water (25 mL) and extracted with CHCI3 (4 x 30 mL). The extracts are dried over MgSθ4 and evaporated. The residue is purified by column chromatography, eluting with 10% CH2CVMeOH. The product-containing fractions are evaporated and the residue is triturated with MeOH to afford the title compound as a brown solid.
  • 7
  • [ 582-33-2 ]
  • [ 959755-46-5 ]
  • [ 959756-23-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-aminobenzoic acid ethyl ester; 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine With hydrogen bromide In water; isopropyl alcohol at 85℃; for 4h; Stage #2: With sodium hydrogencarbonate In water; isopropyl alcohol at 20℃; 1 5,8-Dibromo-[l,2,4]triazolo[l,5-a]pyrazine (1.39 g, 5.00 mmol) and ethyl 3- aminobenzoate (0.93 g, 5.60 mmol) are stirred in 1PrOH (10 mL) and HBr (48% aq., 1.14 mL, 10 mmol) is added. The mixture is heated at 85°C for 4 h and then cooled to rt and quenched with NaHCC"3 (sat. aq., 25 mL). The resulting suspension is cooled to 0°C and the white solid is collected by suction filtration and washed with water (10 mL). The crude product is taken up in EtOH and the solvent evaporated to afford the title compound as an off- white solid (1.79 g, 4.9 mmol) which is used without further purification.
  • 8
  • [ 959755-46-5 ]
  • [ 1195064-72-2 ]
  • [ 1195065-31-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 85℃; Inert atmosphere; 2.1 Compound 2: 4-{8-[4-((1S,4S)-5-Isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamino]-triazolo[1,5-a]pyrazin-5-yl}-furan-2-carboxamide; Step 1: (5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-((1S,4S)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenyl]-amine; 5,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine (2.26 g, 8.14 mmol), 4-((1S,4S)-5-Isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamine (2.07 g, 8.95 mmol, 1.10 equiv.) and DiPEA (4.3 mL, 24.42 mmol, 3.00 equiv.) are mixed in isopropanol (28 mL) under nitrogen. The reaction is heated to 85° C. until completion of the reaction (typically 5 h). The solvent is removed under vacuum and the residue is partitioned between 60 mL aqueous sodium phosphates buffer (pH 7) and 200 mL DCM, the organic layer is washed with 60 1 mL satd. NaCl, dried on anhydrous Na2SO4, filtered and evaporated in vacuo to yield the title compound (3.67 g) as a green-black foamy solid.
  • 9
  • [ 959755-46-5 ]
  • [ 1195065-89-4 ]
  • [ 1195065-91-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine for 70h; Reflux; 27.3 Step 3: 5-Bromo-N-{4-[(1R,4R)-5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl]phenyl}[1,2,4]triazolo[1,5-a]-pyrazin-8-amine (5) To the solution obtained from step 2 is added 5,8-dibromo[1,2,4]triazolo[1,5-a]-pyrazine (1.6 g; 5.8 mmol) and triethylamine (3.4 mL). The resulting mixture was heated at reflux for 70 h, after which the reactor contents were cooled down and filtered to remove solids. The filter cake was washed with 2-MeTHF (2*5 mL) and the filtrate used as such in the next step.
With triethylamine In 2-MeTHF for 70h; Reflux; 2.3 Step 3: 5-Bromo-N-{4-[(1R,4R)-5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl]phenyl}[1,2,4]triazolo[1,5-a]-pyrazin-8-amine (5) To the solution obtained from step 2 is added 5,8-dibromo[1,2,4]triazolo[1,5-a]-pyrazine (1.6 g; 5.8 mmol) and triethylamine (3.4 mL). The resulting mixture is heated at reflux for 70 h, after which the reactor contents are cooled down and filtered to remove solids. The filter cake is washed with 2-MeTHF (2*5 mL) and the filtrate used as such in the next step.
  • 10
  • [ 959755-44-3 ]
  • [ 959755-46-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(3,6-dibromo-pyrazin-2-yl)-N'-hydroxyformamidine With PPA In water at 50 - 70℃; for 2.75h; Stage #2: With sodium hydrogencarbonate 3.3 Step 3: 5,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine (F) N-(3,6-dibromo-pyrazin-2-yl)-N'-hydroxyformamidine (17.4 mg, 58.80 mmol) is treated with polyphosphoric acid (150 g) for one hour at 50° C. and then for 1.75 hours at 70° C. After cooling to room temperature, water is added to the reaction mixture. The resultant suspension is brought to pH 8 by careful addition of solid NaHCO3 in small portions. The precipitate formed is collected by filtration, washed once with 1N NaOH, three times with water and dried in vacuo. The residue is partitioned between ethyl acetate and 1N NaOH and the organic phase is washed one more time with 1N NaOH and once with brine. The organic phase is dried over anhydrous MgSO4, filtered and evaporated to give the title compound (10.15 g) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 8.43 (s, 1H), 8.92 (s, 1H). LCMS: Rt 2.73 min (94.2%), m/z (APCI) 277 (M+H)+.
Stage #1: N-(3,6-dibromo-pyrazin-2-yl)-N'-hydroxyformamidine at 50 - 70℃; for 2.75h; Stage #2: With sodium hydrogencarbonate In water 1.3 Step 3: 5,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine (Intermediate 2) N-(3,6-dibromo-pyrazin-2-yl)-N-hydroxyformamidine (17.4 mg, 58.80 mmol) is treated with polyphosphoric acid (150 g) for one hour at 50° C. and then for 1.75 hours at 70° C. After cooling to room temperature, water is added to the reaction mixture. The resultant suspension is brought to pH 8 by careful addition of solid NaHCO3 in small portions. The precipitate formed is collected by filtration, washed once with 1N NaOH, three times with water and dried in vacuo. The residue is partitioned between ethyl acetate and 1N NaOH and the organic phase is washed one more time with 1N NaOH and once with brine. The organic phase is dried over anhydrous MgSO4, filtered and evaporated to give the title compound (10.15 g) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 8.43 (s, 1H), 8.92 (s, 1H). LCMS: Rt 2.73 min (94.2%), m/z (APCI) 277 (M+H)+.
  • 11
  • [ 959755-46-5 ]
  • [ 1195065-29-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 5 h / 85 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 6 h / 110 °C / Inert atmosphere
  • 12
  • [ 959755-46-5 ]
  • 4-{8-[4-((1S,4S)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-furan-2-carboxamide benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 5 h / 85 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 6 h / 110 °C / Inert atmosphere 3: dichloromethane; methanol
  • 13
  • [ 959755-46-5 ]
  • 4-{8-[4-((1S,4S)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-furan-2-carboxamide citrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 5 h / 85 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 6 h / 110 °C / Inert atmosphere 3: dichloromethane; methanol
  • 14
  • [ 959755-46-5 ]
  • 4-{8-[4-((1S,4S)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-furan-2-carboxamide fumarate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 5 h / 85 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 6 h / 110 °C / Inert atmosphere 3: dimethyl sulfoxide
  • 15
  • [ 959755-46-5 ]
  • 4-{8-[4-((1S,4S)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-furan-2-carboxamide methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 5 h / 85 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 6 h / 110 °C / Inert atmosphere 3: methanol
  • 16
  • [ 959755-46-5 ]
  • 4-{8-[4-((1S,4S)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-furan-2-carboxamide besylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 5 h / 85 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 6 h / 110 °C / Inert atmosphere 3: isopropyl alcohol; water / Reflux
  • 17
  • [ 959755-46-5 ]
  • 4-{8-[4-((1S,4S)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-furan-2-carboxamide edisylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 5 h / 85 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 6 h / 110 °C / Inert atmosphere 3: water; 2,4-dimethylpentan-3-one
  • 18
  • [ 959755-46-5 ]
  • [ 1195065-89-4 ]
  • [ 1195065-85-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / 2-MeTHF / 70 h / Reflux 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 2-MeTHF / 6 h / 80 °C / Inert atmosphere
  • 19
  • [ 959755-46-5 ]
  • 4-((1S,4S)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamine [ No CAS ]
  • [ 1195065-31-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 85℃; for 5h; Inert atmosphere; 2.1 Step 1: (5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-((1S,4S)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenyl]-amine 5,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine (2.26 g, 8.14 mmol), 4-((1S,4S)-5-Isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamine (2.07 g, 8.95 mmol, 1.10 equiv.) and DiPEA (4.3 mL, 24.42 mmol, 3.00 equiv.) are mixed in isopropanol (28 mL) under nitrogen. The reaction is heated to 85° C. until completion of the reaction (typically 5 h). The solvent is removed under vacuum and the residue is partitioned between 60 mL aqueous sodium phosphates buffer (pH 7) and 200 mL DCM, the organic layer is washed with 60 mL satd. NaCl, dried on anhydrous Na2SO4, filtered and evaporated in vacuo to yield the title compound (3.67 g) as a green-black foamy solid.
  • 20
  • [ 959755-42-1 ]
  • [ 959755-46-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydroxylamine hydrochloride / methanol / 16 h / 20 °C 2.1: polyphosphoric acid (PPC) / 2.75 h / 50 - 70 °C 2.2: pH 8
  • 21
  • [ 957346-19-9 ]
  • [ 959755-46-5 ]
  • [ 959755-64-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 8 h / 90 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
  • 22
  • [ 959755-46-5 ]
  • N-ethyl-3-[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydrogen bromide / water; isopropyl alcohol / 4 h / 85 °C 1.2: 20 °C 2.1: dmap / dichloromethane / 2 h / 20 °C 3.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.42 h / 115 °C 4.1: potassium hydroxide; water / tetrahydrofuran / 60 °C 4.2: 0 °C 5.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine / water; N,N-dimethyl-formamide 6.1: hydrogenchloride; water / methanol
  • 23
  • [ 959755-46-5 ]
  • (4-morpholin-4-ylphenyl)-[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 4.5 h / Heating / reflux 2: sodium t-butanolate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 90 °C
  • 24
  • [ 959755-46-5 ]
  • 4-{8-[4-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 8 h / 80 °C 2: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water; N,N-dimethyl-formamide / 90 °C
  • 25
  • [ 959755-46-5 ]
  • 2-methoxy-N-(6-methylpyridin-3-yl)methyl-4-[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen bromide / water; isopropyl alcohol / 24 h / Heating / reflux 2: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 18 h / 85 °C
  • 26
  • [ 959755-46-5 ]
  • 2-methoxy-N-(6-methylpyridin-3-yl)methyl-4-[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-benzamide bis-mesylate salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide / water; isopropyl alcohol / 24 h / Heating / reflux 2: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 18 h / 85 °C 3: methanol; dichloromethane
  • 27
  • [ 959755-46-5 ]
  • [ 959756-24-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogen bromide / water; isopropyl alcohol / 4 h / 85 °C 1.2: 20 °C 2.1: dmap / dichloromethane / 2 h / 20 °C
  • 28
  • [ 959755-46-5 ]
  • [ 959755-56-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 4.5 h / Heating / reflux 2: dichloromethane / 50 °C
  • 29
  • [ 959755-46-5 ]
  • [ 959756-26-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogen bromide / water; isopropyl alcohol / 4 h / 85 °C 1.2: 20 °C 2.1: dmap / dichloromethane / 2 h / 20 °C 3.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.42 h / 115 °C 4.1: potassium hydroxide; water / tetrahydrofuran / 60 °C 4.2: 0 °C
  • 30
  • [ 959755-46-5 ]
  • [ 959756-25-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogen bromide / water; isopropyl alcohol / 4 h / 85 °C 1.2: 20 °C 2.1: dmap / dichloromethane / 2 h / 20 °C 3.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.42 h / 115 °C
  • 31
  • [ 959755-46-5 ]
  • C22H24N8O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrogen bromide / water; isopropyl alcohol / 4 h / 85 °C 1.2: 20 °C 2.1: dmap / dichloromethane / 2 h / 20 °C 3.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.42 h / 115 °C 4.1: potassium hydroxide; water / tetrahydrofuran / 60 °C 4.2: 0 °C 5.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine / water; N,N-dimethyl-formamide
  • 32
  • N'-(3,6-dibromo-pyrazin-2-yl)-N,N-dimethylformamidine [ No CAS ]
  • [ 959755-46-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydroxylamine hydrochloride / methanol / 16 h / 20 °C 2.1: PPA / 2.75 h / 50 - 70 °C 2.2: 20 °C / pH 8
  • 33
  • [ 959755-46-5 ]
  • 5-(4-amino-2-methylphenyl)-N-cyclopropyl-[1,2,4]triazolo[1,5-a]pyrazin-8-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 3 h
  • 34
  • [ 959755-46-5 ]
  • 1-(3-(tert-butyl)-1-phenyl-1H-pyrazol-5-yl)-3-(4-(8-(cyclopropylamino)[1,2,4]triazolo[1,5-a]pyrazin-5-yl)-3-methylphenyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 3 h 3: dimethyl sulfoxide / 14 h / 60 °C
  • 35
  • [ 959755-46-5 ]
  • 1-(3-(tert-butyl)-1-(3-nitrophenyl)-1H-pyrazol-5-yl)-3-(4-(8-(cyclopropylamino)[1,2,4]triazolo[1,5-a]pyrazin-5-yl)-3-methylphenyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 3 h 3: dimethyl sulfoxide / 14 h / 60 °C
  • 36
  • [ 959755-46-5 ]
  • 1-(3-(tert-butyl)-1-(3-chlorophenyl)-1H-pyrazol-5-yl)-3-(4-(8-(cyclopropylamino)[1,2,4]triazolo[1,5-a]pyrazin-5-yl)-3-methylphenyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 3 h 3: dimethyl sulfoxide / 14 h / 60 °C
  • 37
  • [ 959755-46-5 ]
  • 1-(3-(tert-butyl)-1-(3-cyanophenyl)-1H-pyrazol-5-yl)-3-(4-(8-(cyclopropylamino)[1,2,4]triazolo[1,5-a]pyrazin-5-yl)-3-methylphenyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 3 h 3: dimethyl sulfoxide / 14 h / 60 °C
  • 38
  • [ 959755-46-5 ]
  • [ 765-30-0 ]
  • 5-bromo-N-cyclopropyl-[1,2,4]triazolo[1,5-a]pyrazin-8-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With N-ethyl-N,N-diisopropylamine In 1,4-dioxane 2.20.1 5.1.2.20.1 Step 1.5-Bromo-N-cyclopropyl-[1,2,4]triazolo[1,5-a]pyrazin-8-amine (19) A mixture of the known compound 18 (1.5g, 6.43mmol), cyclopropylamine (2.23mL, 32.13mmol) and N, N-diisopropylethylamine (2.24mL, 12.85mL) in 1,4-dioxane (20mL) was stirred at 120°C for 20h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with brine. The organic phase was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (Hexanes: EtOAc=10:1) to afford the title compound 19 (1.62g, 99%). 1H NMR (300MHz, CDCl3) δ 8.29 (s, 1H), 7.76 (s, 1H), 6.09 (bs, 1H), 2.96-2.89 (m, 1H), 0.98-0.91 (m, 2H), 0.71-0.66 (m, 1H).
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