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Chemical Structure| 1034618-02-4 Chemical Structure| 1034618-02-4

Structure of 1034618-02-4

Chemical Structure| 1034618-02-4

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Product Details of [ 1034618-02-4 ]

CAS No. :1034618-02-4
Formula : C12H16F3N3O
M.W : 275.27
SMILES Code : NC1=CC(N2CCN(C)CC2)=CC=C1OC(F)(F)F
MDL No. :MFCD25954605

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Application In Synthesis of [ 1034618-02-4 ]

* 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 [ 1034618-02-4 ]

[ 1034618-02-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 109-01-3 ]
  • [ 886762-08-9 ]
  • [ 1034618-02-4 ]
YieldReaction ConditionsOperation in experiment
64% With lithium hexamethyldisilazane;tris-(dibenzylideneacetone)dipalladium(0); DavePhos; In tetrahydrofuran; for 1h;Heating / reflux; Example 35; N-[5-(4-Methyl-piperazin-l-yl)-2-trifluoromethoxy-phenyl]-guanidine; Step 1. 5-(4-Methyl-piperazin-l-yl)-2-trifluoromethoxy-phenylamine; Tris(dibenzilideneacetone)dipalladium, Pd2(dba)3 (1.1 g, 1.2 mmol), 2- dicyclohexylphosphino-2'-(N,N-dimethylamino)-biphenyl (0.94 g, 2.4 mmol), 5- bromo-2-trifluoromethoxy-phenylamine (30.7 g, 120 mmol) in THF (50 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. LiN(TMS)2 solution (IM in THF, 288 mL) and N- methylpiperazine (26.7 mL, 194 mmol) were added and the reaction refluxed for 1 h. The reaction mixture was then allowed to cool to room temperature and filtered through a pad of celite. The organic phase was concentrated, the residue dissolved inDCM (200 ml) and washed with water (1 x 100 ml). The organic phases were dried over anhydrous Na2SO4, the solvent evaporated in vacuo and the crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10) to afford 21.1 g of 5-(4-methyl-piperazin- 1 -yl)-2-trifluoromethoxy-phenylamine (64% yield) as a light brown powder.1H NMR (400 MHz, DMSO-J6) delta ppm 2.23 (s, 3 H) 2.42 - 2.47 (m, 4 H) 3.02 - 3.08 (m, 4 H) 5.10 (s, 2 H) 6.16 (dd, J=8.90, 2.93 Hz, 1 H) 6.33 (d, J=2.93 Hz, 1 H) 6.90 (dd, J=8.90, 1.46 Hz, I H).
  • 2
  • [ 755039-55-5 ]
  • [ 1034618-02-4 ]
  • [ 1159994-47-4 ]
YieldReaction ConditionsOperation in experiment
22% To a suspension of (R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydro-5H- pteridin-6-one (0.60 g, 2 mmol), prepared as described in WO 2004/076454, in a 2/1 mixture E^O/Ethanol (60 mL), were added 37%HC1 (0.6 mL) and 2-trifluoromethoxy-5-(4-Methyl-piperazin-l-yl)-phenylamine (0.55 g, 2 mmol), prepared as described inPreparation 1. The reaction was refluxed for 72 hours, concentrated to small volume(20 mL) diluted with water (30 mL) and extracted with DCM (2 X 50 mL). The aqueous phase was neutralized by addition of NaHCCh then extracted with DCM (2 X 50 mL).The organic fractions were combined, dried over sodium sulfate and solvent was evaporated to drieness. Purification of crude solid by flash chromatography on silica gel <n="22"/>(eluant: DCM/EtOH 90/10) yield the title compound as an light brown solid (0.23 g ,22% yield).1H NMR (400 MHz, DMSO-J6) delta ppm 0.76 (t, J=7.50 Hz, 3 H) 1.44 (m, 2H) 1.60 (m,2H) 1.73 (m, 2H) 1.82 (m, 4H) 2.27 (s, 3 H) 2.49 - 2.53 (m, 4 H) 3.09 - 3.18 (m, 4 H) 3.23 (s, 3 H) 4.18 (dd, J=7.56, 3.66 Hz, 1 H) 4.20 - 4.28 (m, 1 H) 6.67 (dd, J=9.15, 3.05Hz, 1 H) 7.12 - 7.21 (m, 1 H) 7.54 (d, J=3.05 Hz, 1 H) 7.77 (s, 1 H) 7.93 (s, 1 H); MS(ESI): 534 [M+H]+.
 

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