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Chemical Structure| 157373-27-8 Chemical Structure| 157373-27-8

Structure of 157373-27-8

Chemical Structure| 157373-27-8

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Product Details of [ 157373-27-8 ]

CAS No. :157373-27-8
Formula : C13H13Cl2NO4
M.W : 318.15
SMILES Code : O=C(OCC)/C(C(C1=C(Cl)N=C(Cl)C=C1)=O)=C/OCC

Safety of [ 157373-27-8 ]

Application In Synthesis of [ 157373-27-8 ]

* 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 [ 157373-27-8 ]

[ 157373-27-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 157373-27-8 ]
  • [ 344-19-4 ]
  • C19H16Cl3FN2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h; To a solution of 6.07 g (19.1 mmol) of ethyl 2-[(2,6-dichloropyridin-3-yl)carbonyl]-3-ethoxyacrylate (CAS 157373-27-8) and 4.81 g (26.7 mmol) of <strong>[344-19-4]2,6-dichloro-4-fluoroaniline</strong> in 30 ml DCM were added 23.3 ml (134 mmol) of DIPEA, and the mixture was stirred at RT for 4 h. Subsequently, 2.64 g (19.1 mmol) of potassium carbonate were added and the mixture was heated under reflux overnight. The mixture was diluted with 200 ml of DCM and washed twice with 75 ml of 1 M aqueous hydrochloric acid. The organic phase was dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. The suspension obtained was stirred with 40 ml of tert-butyl methyl ether, and the precipitate was filtered off with suction, washed with 10 ml of tert-butyl methyl ether and dried under high vacuum. 3.81 g (45% of theory, 94% purity) of the title compound were obtained. LC-MS (Method 1): Rt=1.04 min; MS (ESIpos) m/z 415 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=8.88 (s, 1H), 8.65 (d, 1H), 7.92 (d, 2H), 7.69 (d, 1H), 4.25 (q, 2H), 1.28 (t, 3H).
  • 2
  • [ 159783-22-9 ]
  • [ 157373-27-8 ]
  • ethyl 7-chloro-1-(3,5-difluoropyridin-4-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% 4.7 ml (26.7 mmol) of DIPEA were added to a solution of 1.22 g (3.82 mmol) of ethyl 2-[(2,6-dichloropyridin-3-yl)carbonyl]-3-ethoxyacrylate (CAS 157373-27-8) and 696 mg (5.35 mmol) of <strong>[159783-22-9]3,5-difluoropyridin-4-amine</strong> in 10 ml of dichloromethane, and the mixture was stirred at RT for 4 h. 528 mg (3.82 mmol) of potassium carbonate were then added, and the mixture was heated under reflux overnight. The mixture was diluted with 100 ml of DCM and washed three times with 20 ml of 1 M aqueous hydrochloric acid and extracted once with saturated aqueous sodium chloride solution. The organic phase was dried over magnesium sulfate and filtered, and the solvent was removed under reduced pressure. The residue was purified in a silica gel cartridge (dichloromethane/methanol). The solvents were evaporated under reduced pressure and the residue was purified directly by preparative RP-HPLC (column: Reprosil 250*30; 10mu, flow rate: 50 ml/min, acetonitrile/water; 0.1% trifluoroacetic acid). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 203 mg (15% of theory, purity 100%) of the title compound. LC-MS (Methode 2): Rt=1.55 min; MS (ESIpos): m/z=366 [M+H]+. 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=8.99 (s, 1H), 8.91 (s, 2H), 8.63 (d, 1H), 7.70 (d, 1H), 4.25 (q, 2H), 1.27 (t, 3H).
  • 3
  • [ 159783-22-9 ]
  • [ 157373-27-8 ]
  • 7-chloro-1-(3,5-difluoropyridin-4-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid [ No CAS ]
 

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