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Chemical Structure| 1092523-24-4 Chemical Structure| 1092523-24-4

Structure of 1092523-24-4

Chemical Structure| 1092523-24-4

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Product Details of [ 1092523-24-4 ]

CAS No. :1092523-24-4
Formula : C12H13ClN4O2
M.W : 280.71
SMILES Code : O=C(C1=C(N)N(CC)C2=C(C=CC(Cl)=N2)C1=O)NC
MDL No. :MFCD22571280

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Application In Synthesis of [ 1092523-24-4 ]

* 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 [ 1092523-24-4 ]

[ 1092523-24-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 42841-64-5 ]
  • [ 1092523-24-4 ]
  • [ 1092538-80-1 ]
YieldReaction ConditionsOperation in experiment
65% A suspension of 3 g (10.69 mmol) of 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamide in 20 ml of a DMF/Et3N mixture (V/V; 1/1) is placed in an 80 ml microwave tube. This suspension is sparged with argon for 10 minutes and then 1.83 g of (+-)-1-methoxy-2-methyl-3-butyn-2-ol (16.03 mmol), 0.081 g of CuI (0.43 mmol) and 0.375 g of bis(triphenylphosphine) palladium(II)dichloride (0.53 mmol) are successively added. The sealed tube is placed in a microwave oven (CEM apparatus, Discover model) and the mixture is heated under pressure at 90 C. for 60 minutes (P=100 W) and then cooled and evaporated to dryness. The residue is taken up in an ethyl acetate/THF mixture and then washed with a 0.1N aqueous HCl solution. The organic phase is dried over sodium sulphate, filtered, and concentrated under vacuum. The residue obtained is purified by silica chromatography (solid deposit; elution with a cyclohexane:ethyl acetate gradient, 30:70 to 20:80). 2.49 g of the expected product are obtained in the form of a pale yellow solid. The product can be recrystallized from ethanol, so as to give white crystals. Melting point=211 C. MH+=358. Yield=65%. 1H NMR (DMSO-d6, 400 MHz, delta in ppm): delta 11.75 (s, <1H, very broad); 11.00 (q, 1H, broad); 8.45 (d, 1H); 8.00 (s, 1H, broad); 7.4 (d, 1H); 5.8 (s, 1H); 4.4 (q, 2H); 3.5-3.3 (m+s, 5H); 2.8 (d, 3H); 1.45 (s, 3H); 1.2 (t, 3H).
  • 2
  • [ 1092523-24-4 ]
  • [ 380430-57-9 ]
  • [ 1314069-30-1 ]
YieldReaction ConditionsOperation in experiment
93% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,2-dimethoxyethane; ethanol; water; at 110℃; for 3h;Inert atmosphere; 4.2: 2-amino-1-ethyl-N-methyl-7-{4-[(methylsulfonyl)amino]phenyl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide [0255] 0.33 g (1.16 mmol) of chloronaphthyridine obtained at the end of step 1.6 is dissolved in 16 ml of dimethoyethane and 8 ml of ethanol and nitrogen is bubbled through. The boronic acid obtained at the end of the preceding step as well as 8 ml of a saturated aqueous NaHCO3 solution are added. 67 mg (0.06 mmol) of tetrakis(triphenylphosphine)palladium(0) are introduced and the medium is heated at 110 C. for 3 h. After cooling, the mixture is filtered on paper and the filtrate is concentrated to dryness. The residue is taken up in water and the precipitate obtained is filtered, washed with water and dried in an oven under vacuum over P2O5 and then purified by chromatography on silica (eluent: CH2Cl2/MeOH: 95/5). 450 mg of product are obtained in the form of a powder. Yield: (93%). Melting point: >300 C. [0256] 1H NMR (200 MHZ, DMSO-d6): delta (ppm): 1.3 (t; 3H; 7 Hz); 2.8 (d; 3H, 4.5 Hz); 3.1 (s; 3H); 4.6 (q; 2H; 7 Hz); 7.3 (d; 2H; 8 Hz); 7.9 (d; 1H; 8 Hz); 8.2 (d; 2H; 8 Hz); 8.50 (d; 1H; 8 Hz); 10.1 (s; 1H); 11.1 (q; 1H, 4.5 Hz); 11.7 (br s; 1H). [0257] MH+: 416 (tr: 5.05 min, condition B).
 

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