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Chemical Structure| 7597-22-0 Chemical Structure| 7597-22-0

Structure of 7597-22-0

Chemical Structure| 7597-22-0

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Product Details of [ 7597-22-0 ]

CAS No. :7597-22-0
Formula : C11H16ClN5O2
M.W : 285.73
SMILES Code : ClC1=NC(N2CCOCC2)=NC(N3CCOCC3)=N1
MDL No. :MFCD00432885
InChI Key :WYCCBNGHFYBVOM-UHFFFAOYSA-N
Pubchem ID :224967

Safety of [ 7597-22-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 7597-22-0 ]

* 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 [ 7597-22-0 ]

[ 7597-22-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 7597-22-0 ]
  • [ 214360-73-3 ]
  • [ 1197159-91-3 ]
YieldReaction ConditionsOperation in experiment
88% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 5h;Reflux; The mixture of 2-chloro-4,6-dimorpholin-4-yl-[1,3,5]triazine (2, 30 g, 0.105 mol) 4-aminophenylboronic acid pinacol ester (3, 25.7 g, 0.117 mol, Boron Molecular), sodium carbonate (23 g , 0.21 mol) and tetrakistriphenylphosphine palladium (1 g, O.deltawt % Aldrich) in water (150 ml) and dimethoxyethane (DME, 450 ml) was heated at reflux for 5 hours. The reaction mix was cooled to the room temperature and filtered through paper filter. The layers of the filtrate were separated, the organic layer was washed with brine and concentrated. The residue was dissolved in methylene chloride, washed with brine, dried over sodium sulfate and concentrated. The solids were triturated with diethyl ether, filtered, and air dried to give the beige solids (31.5 g, 0.092 mol). Yield 88%; Mass: 343.1 (M+H)+.
83% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 24h;Reflux; A mixture of 2-chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine (1.4 g, 4.9 mmoles), a catalytic amount of tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.061 mmoles), sodium carbonate solution 2 M (3 mL), 4-aminophenylboronic acid pinacol ester (1.6 g, 7.3 mmoles) and DME (100 mL) was refluxed for 24 hours. The solvent was evaporated, and the residue was dissolved in methylene chloride and filtered through Celite. The filtrate was washed with water (200 mL) and the organic layer was dried with magnesium sulfate. This was filtered and the solvent was evaporated. The residue was purified by Silica gel column chromatography and eluted with Ethyl acetate/hexanes (1:1) to give 1.40 g, (83% yield) of 4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)aniline as an amorphous solid. (M+H) 343.
83% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; for 24h;Reflux; A mixture of 2-chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine (1.4 g, 4.9 mmoles), a catalytic amount of tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.061 mmoles), sodium carbonate solution 2 M (3 mL), 4-aminophenylboronic acid pinacol ester (1.6 g, 7.3 mmoles) and DME (100 mL) was refluxed for 24 hours. The solvent was evaporated, and the residue was dissolved in methylene chloride and filtered through Celite. The filtrate was washed with water (200 mL) and the organic layer was dried with magnesium sulfate. This was filtered and the solvent was evaporated. The residue was purified by Silica gel column chromatography and eluted with Ethyl acetate/hexanes (1:1) to give 1.40 g, (83% yield) of 4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)aniline as an amorphous solid. (M+H) 343.
76% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; for 5h;Inert atmosphere; Reflux; 4-(4-chloro-6-morpholino-l,3,5-triazin-2-yl)morpholine (7 g, 24.50 mmol), 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (6.00 g, 27.37 mmol), sodium carbonate (5.37 g, 50.71 mmol), and Tetrakis (233.33 mg, 201.92 umol) were charged in a round bottom flask and dissolved in a mixture of water (30.62 mL) and DME (91.87 mL) under a nitrogen atmosphere. The reaction was heated to reflux for 5 hours and cooled to room temperature. Two layers were visible and the organic layer was collected, washed with brine (1 x 25 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated, and the remaining residue was resuspended in DCM (100 mL) and washed with brine (2 x 50 mL) before being dried over anhydrous sodium sulfate and concentrated under reduced pressure. The remaining solid was triterated with MTBE (50 mL) and filtered to give 6.4 g of Compound 17A (76%) as an off-white solid (M+H = 343.2)
73.5% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; for 24h;Reflux; Inert atmosphere; Synthetic method: 4,4'-(6-chloro-1,3,5-triazine-2,4-diyl)bismorpholine (3.0 g, 10.52 mmol) was dissolved in DME (30 mL) and added sequentially. Pd(PPh3)4 (0.12g, 0.10mmol), 2.0M Na2CO3 solution (6.40mL) and 4-aminoPhenylboronic acid pinacol ester (3.46 g, 15.78 mmol) was refluxed for 24 h under N2. Evaporate the solvent under reduced pressure and dissolve the residueIn CH 2 Cl 2 (50 mL), it was washed twice with water (50 mL×2), once with saturated NaCl (30 mL), and dried over anhydrous Na 2 SO 4 . Steaming under reduced pressureThe solvent and the residue were separated by column chromatography, eluent: EA/PE = 1/1 to give the desired product 2.65 g, yield: 73.50%.
52% With tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 110℃; for 24h;Inert atmosphere; General procedure: A mixture of compound 7a (5 mmol), 4-aminophenylboronic acid pinacol ester (10 mmol), Pd(Ph3P)4 (0.1 mmol), Na2CO3 (10 mmol) in 1,4-dioxane/H2O (20 mL) was stirred at 110 C for 24 h under Ar. The reaction mixture was filtered through celite. The filtrate was concentrated in vacuo and then extracted with EtOAc. The organic layer was evaporated to give a residue, which was purified by chromatography (petroleum ether/EtOAc, 5:1) to give pure product as a yellow solid, yield 59%.

  • 2
  • [ 7768-28-7 ]
  • [ 7597-22-0 ]
  • [ 96042-30-7 ]
  • [ 1269626-25-6 ]
YieldReaction ConditionsOperation in experiment
15% With sodium hydride; In tetrahydrofuran; n-heptane; mineral oil; Route 4 (Route 3 See Example 12).2-[2-(4,6-Di-morpholin-4-yl-[1,3,5]triazin-2-yloxy)-ethyl]-phenol2-(2-Hydroxy-ethyl)-phenol (73 mg, 0.53 mmol) was added to a solution of 2-chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine (151 mg, 0.53 mmol) in THF (3 ml) followed by sodium hydride (60percent suspension in mineral oil; 14 mg, 1.06 mmol) and the mixture was stirred at room temperature for 1 h and heated at 70° C. for 18 h.After cooling, the mixture was partitioned between water and EtOAc and the aqueous phase was extracted with EtOAc.The combined organic phases were dried (MgSO4) and concentrated in vacuo.The crude residue was purified by column chromatography with EtOAc/heptane (0-40percent gradient) as the eluent followed by trituration from DCM/heptane to give the title compound (30 mg, 15percent).
  • 3
  • [ 7597-22-0 ]
  • [ 89415-43-0 ]
  • [ 1197159-91-3 ]
  • 4
  • [ 7597-22-0 ]
  • [ 330793-01-6 ]
  • [ 1197159-91-3 ]
 

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