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Chemical Structure| 175201-98-6 Chemical Structure| 175201-98-6

Structure of 175201-98-6

Chemical Structure| 175201-98-6

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Product Details of [ 175201-98-6 ]

CAS No. :175201-98-6
Formula : C9H9ClN4O
M.W : 224.65
SMILES Code : O=C(C1=CN=C(N(C)N=C2C)C2=C1Cl)N
MDL No. :MFCD00067963

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Application In Synthesis of [ 175201-98-6 ]

* 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 [ 175201-98-6 ]

[ 175201-98-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 6299-67-8 ]
  • [ 175201-98-6 ]
  • 4-(2,3-dimethoxy-phenylamino)-1,3-dimethyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine-5-carboxylic acid amide [ No CAS ]
  • 3
  • [ 79-37-8 ]
  • [ 106-47-8 ]
  • [ 175201-94-2 ]
  • [ 175201-98-6 ]
  • N-(4-Chloro-1,3-dimethylpyrazolo[5,4-b]pyridin-5-yl)-N-[(4-chlorophenyl)-amino]carbiy}carboxamide [ No CAS ]
  • N-(4-Chloro-1,3-dimethyl-pyrazolo[5,4-b]pyridin-5-yl)-N-[(4-chlorophenyl)-amino]carbonyl}carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide; ammonia; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; Example 1 N-(4-Chloro-1,3-dimethylpyrazolo[5,4-b]pyridin-5-yl)-N-[(4-chlorophenyl)-amino]carbiy}carboxamide (39) Oxalyl chloride (4.5 mL of a 2M solution in dichloromethane) was added dropwise to a stirred suspension of <strong>[175201-94-2]4-chloro-1,3-dimethylpyrazolo [5,4-b]pyridine-5-carboxylic acid</strong> (0.98 g) in anhydrous dichloromethane (14 mL), followed by 4 drops of N,N-dimethylformamide (DMF). After the evolution of gas subsided, 4 more drops of DMF were added, and this operation was repeated three more times. The mixture was stirred at room temperature for 45 min, filtered to remove trace amounts of insoluble material, and the solvent evaporated under reduced pressure. The residue was dried under high vacuum for 1 h, cooled in an ice-bath, and treated with ammonium hydroxide (28% NH3 in water, 20 mL) in an exothermic reaction. The mixture was stirred at 0 C. for 30 min, and at room temperature for an additional 1 h. The solid was collected by filtration, washed with water, and dried under vacuum to give the carboxamide as a white powder. Oxalyl chloride (1.4 mL of a 2M solution in dichloromethane) was added dropwise to a suspension of 4-chloro-1,3-dimethylpyrazolo[5,4-b] pyridine-5-carboxamide (0.41 g) in anhydrous dichloromethane (5 mL). The mixture was heated at reflux for 15 h, and cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was dissolved in anhydrous THF (6 mL). An aliquot of this solution (1.5 mL) was added dropwise to an ice-cooled solution of 4-chloroaniline (57 mg) in anhydrous THF (2 mL). The ice-bath was removed and the mixture was stirred at room temperature for 1.5 h. The precipitated solid was collected by filtration, washed with dichloromethane and methanol, and dried under high vacuum to afford N-(4-Chloro-1,3-dimethyl-pyrazolo[5,4-b]pyridin-5-yl)-N-[(4-chlorophenyl) amino]carbonyl}carboxamide as a white powder. 1H NMR (300 MHz, DMSO-d6) delta 2.68 (s, 3H), 4.02 (s, 3H), 7.42 (d, 2H, J=8.7 Hz), 7.64 (d, 2H, J=8.7 Hz), 8.69 (s, 1H), 10.47 (s, 1H), 11.37 (s, 1H), MS (API-Cl) m/z 340, 342, 344.
 

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