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Chemical Structure| 867330-72-1 Chemical Structure| 867330-72-1

Structure of 867330-72-1

Chemical Structure| 867330-72-1

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Product Details of [ 867330-72-1 ]

CAS No. :867330-72-1
Formula : C15H13ClN4O
M.W : 300.74
SMILES Code : NC1=NC2=C(C)C=C(C3=CC(OC)=CC=C3Cl)C=C2N=N1
MDL No. :MFCD12024680

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Application In Synthesis of [ 867330-72-1 ]

* 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 [ 867330-72-1 ]

[ 867330-72-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 867330-26-5 ]
  • [ 89694-46-2 ]
  • [ 867330-72-1 ]
YieldReaction ConditionsOperation in experiment
84% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; for 4h;Heating / reflux; Example 50 Synthesis of 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine 7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine (33.47 mmol, 1.0 equiv), 1-chloro-4-methoxy-2-boronic acid (50.21 mmol, 1.5 equiv), Pd(PPH3)4 (3.347 mmol, 0.1 equiv), and Na2CO3 (133.9 mmol, 4.0 equiv) dissolved in DME/EtOH/water 6:1:1 and refluxed at 100° C. under an argon blanket for 4 h. The reaction was cooled to room temperature and diluted with 100 mL DCM and filtered. Precipitate recovered was suspended in water, filtered and rinsed with ether. Precipitate afforded product: 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine, a green solid (8.37 g, 84percent yield). Rf=0.85 (9:1 DCM/MeOH). 1H NMR (DMSO-d6): delta 3.35 (s, 6H), 7.01 (dd, J=8.8 Hz, J=3.0, 1H), 7.09 (d, J=3.0 Hz, 1H), 7.48 (d, J=8.8 Hz, 1H), 7.75 (bm, 2H). MS (ES+) m/z=303. LC retention time 3.03 min.
  • 2
  • [ 867330-72-1 ]
  • [ 837-12-7 ]
  • [7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With potassium tert-butylate;palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; for 18h;Heating / reflux; 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine (1.0 equiv., 0.75 mmol), <strong>[837-12-7]1-(4-bromo-benzenesulfonyl)-4-methyl-piperazine</strong> (1.5 equiv., 1.125 mmol), Xantphos (0.1 equiv., 0.074 mmol), palladium acetate (0.05 equiv., 0.0375 mmol), and potassium-tert-butoxide (2.0 equiv, 1.5 mmol) were dissolved in 20 mL of dioxane and bubbled with argon. The reaction was stirred in an oil bath at 100 C. for 18 h under an argon blanket. The reaction was cooled to room temperature and filtered to remove inorganics, concentrated under reduced pressure, then brought up in EtOAc and extracted using saturated NaHCO3 and brine. The organics were dried over Na2SO4 and concentrated under reduced pressure then precipitated using EtOAc/Hexanes (1:5 v/v) to afford brown solid (182.3 mg, 45% yield). MS (ES+): m/z=540 LC retention time: 2.67 min.
  • 3
  • [ 867330-72-1 ]
  • [ 127116-19-2 ]
  • C26H29ClN8O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With potassium tert-butylate;palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; DMF (N,N-dimethyl-formamide); at 160℃; for 0.333333h;Irradiated with microwave; Example 146 Synthesis of 4-chloro-3-(3-{6-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-2-methyl-pyrimidin-4-ylamino}-5-methyl-benzo[1,2,4]triazin-7-yl)-phenol To synthesize the title compound (CLXX), an intermediate compound 64 (2-(4-{6-[7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-2-methyl-pyrimidin-4-yl}-piperazin-1-yl)-ethanol) shown below was used. To synthesize compound 64, a suspension of compound 16 (scheme (CXXXV), Example 124) (0.10 g, 0.33 mmol), compound 53 (Example 145) (0.10 g, 0.39 mmol), Pd(OAc)2 (5 mg, 0.022 mmol), Xantphos (26 mg, 0.045 mmol) and potassium tert-butoxide (80 mg, 0.71 mmol) in dioxane/DMF (2.5 mL, 4/1 v/v) was sealed in a microwave reaction tube and irradiated with microwave at 160 C. for 20 min. After cooling down to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (5-10% MeOH/DCM) to yield compound 64 as a yellow solid (43 mg, 25%). MS (ESI+): m/z 521.
 

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