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Chemical Structure| 1352830-76-2 Chemical Structure| 1352830-76-2

Structure of 1352830-76-2

Chemical Structure| 1352830-76-2

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Product Details of [ 1352830-76-2 ]

CAS No. :1352830-76-2
Formula : C5H4ClFN2
M.W : 146.55
SMILES Code : FC1=CC(N)=CC(Cl)=N1
MDL No. :MFCD24644979

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Application In Synthesis of [ 1352830-76-2 ]

* 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.

  • Upstream synthesis route of [ 1352830-76-2 ]
  • Downstream synthetic route of [ 1352830-76-2 ]

[ 1352830-76-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1352830-73-9 ]
  • [ 1352830-76-2 ]
  • [ 63489-58-7 ]
YieldReaction ConditionsOperation in experiment
37%
Stage #1: With potassium fluoride; [2.2.2]cryptande In dimethyl sulfoxide at 160℃; for 72 h;
Stage #2: With hydrogenchloride In methanol for 1 h;
Anhydrous F (300 mg, 5. 16 mmol) was added to a mixture of 1 (700 mg, 1.72 mmol) and kryptofix (1.0 g, 2.65 mmol) in DM SO (2.5 mL) and the mixture was stirred at 160 °C for 72 h. After the reaction, water was added and the solid formed was filtered and dried. The solid was dissolved in ethyl acetate (25.0 mL) and washed with water and dried (Na2S04). Evaporation of the solvent gave a dark oil, which was purified by silica gel column chromatography using hexane /ethyl acetate (7/3). UV visible fractions were collected and evaporated to give an yellow oil, which solidified on standing. Yield 0.5 g. (88percent). This was found to be a mixture of 63, 64 and 62 in the ratio (13:51 : 14) by HPLC analysis. A portion of the solid (80.0 mg) was purified by preparative HPLC using CH3CN / water /0.1percent TFA. Fractions containing the pure product were collected and evaporated to give the compound 64 as a while solid. Yield 32.0 mg (42percent). MS: 389.2 (M+H)+. The trityl derivatives 63, 63 and 64 obtained in the above reaction (600 mg, 1.5 mmol) was dissolved in methanolic HQ (5.0 inL) and stirred for 1 h. Methanol was removed and the residue was triturated with ethyl acetate to remove the trityl chloride and the resulting hydrochloride was dissolved in methanol and stirred with anion exchange resin. The pH of the solution (7.0) tested and the methanolic solution was filtered and concentrated to give the free amine mixture 65, 66 and 61. Yield 200 mg (89percent). A portion of the solid (38.0 mg) was purified by preparative HPLC (Ci8 column (0.46 x 5 cm, gradient 0- 1 0 percent) CH3CN / water/ 0.1 percent) TFA. Fractions containing the pure product were collected and concentrated to give the compound 65. Yield 10.0 mg (37percent). MS: (M+H f 147.0. 1HNMR (DMSO-d6) d 6.06 (s, I H ).6.46 (s, 1 H ). 6.80 (bs, 2H).
References: [1] Patent: WO2011/159864, 2011, A1, . Location in patent: Page/Page column 41-42.
  • 2
  • [ 2587-02-2 ]
  • [ 1352830-76-2 ]
  • [ 63489-58-7 ]
References: [1] Patent: WO2011/159864, 2011, A1, .
 

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