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Chemical Structure| 6531-04-0 Chemical Structure| 6531-04-0

Structure of 6531-04-0

Chemical Structure| 6531-04-0

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Product Details of [ 6531-04-0 ]

CAS No. :6531-04-0
Formula : C5H2Cl2N2O
M.W : 176.99
SMILES Code : O=C(Cl)C1=NN=C(Cl)C=C1
MDL No. :MFCD09991889

Safety of [ 6531-04-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H335-H314
Precautionary Statements:P260-P264-P270-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P403+P233-P405-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 6531-04-0 ]

* 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 [ 6531-04-0 ]

[ 6531-04-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 6531-04-0 ]
  • [ 65202-50-8 ]
YieldReaction ConditionsOperation in experiment
65% With methanol; In dichloromethane; at 0℃; for 1h; PREPARATION 58 6-Chloro-pyridazine-3-carboxylic acid methyl ester Oxalyl chloride (1.14mL, 13.09mmol), was added dropwise to an ice-cold suspension of 6-CHLORO-PYRIDAZINE-3-CARBOXYLIC acid [(1.9g, 11.9mmol), J. Het. Chem. 29 (6), 1583-92,. 1992] in a mixture of DICHBROMETHANE (50ML) AND N, N-dimethylformamide (1 drop) and the mixture was stirred for 1 hour at room temperature. The reaction mixture was then evaporated under reduced pressure and the residue was diluted with dichloromethane (30ML) and cooled to 0°C. Methanol (485muL, 11.9mmol) was added and the mixture was stirred at 0°C for 1 hour. Sodium hydrogen carbonate solution was then added to the reaction mixture and the aqueous layer was separated and extracted with DICHLOROMETHANE (X2).. The combined organic solutions were washed with brine, - dried over-sodium sulfate and concentrated in. vacuo to afford the title compound as a white solid in 65percent yield, 1.33g. .-IHNMR (CDCL3, 400MHZ) No.: 4.09 (s, 3H),-7. 67 (d, 1H), 8.16(d, 1H). MS APCI+ m/z 173 [MH]+
  • 2
  • [ 67-56-1 ]
  • [ 6531-04-0 ]
  • [ 65202-50-8 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; ethyl acetate; for 0.25h; Step 2; Methyl 6-chloropyridazine-3-carboxylate; To a suspension of 6-chloropyridazine-3-carboxylic acid (4.2 g, 26.5 mmol) in a mixture of dichloromethane (100 mL) and ethyl acetate (30 mL) and a few drops of DMF was added oxalyl chloride (3 mL, 34 mmol). The mixture was stirred at room temperature for 4 h until solution was attained, then quenched with 20 mL of methanol. After 15 min, the mixture was concentrated, and the resulting solid was swirled in ether and filtered. The solid was triturated with dichloromethane and the filtrate was evaporated to provide the title compound.
With triethylamine; for 0.5h; Oxalyl chloride (21.3 mL, 252 mmol) was added to a solution of 6-chloropyridazine-3- carboxylic acid (20.0 g, 126 mmol) in DCM (500 mL) at 25 °C, and the resulting mixture was stirred for 1 h, then concentrated. A solution of triethylamine (17.5 mL, 126 mmol) in MeOH (500 mL) was added to the residue, and the mixture was stirred for 30 min. The product mixture was concentrated and residue was partitioned between EtOAc (500 mL) and water (100 mL). The organic layer was dried over Na2SC>4 and concentrated. The residue was suspended in MTBE,filtered and dried to give the title compound. MS: m/z = 173 (M + 1). NMR (400 MHz, CDC13) delta 8.17 (d, / = 8.8 Hz, 1H), 7.68 (d, / = 8.8 Hz, 1H), 4.09 (s, 3H).
In dichloromethane; at 0 - 10℃; for 1h; Step 2: Methyl 6-chlorop yridazine-3 -carboxylate; To a suspension of -chloropyridazine-S-carboxylic acid (4.2 g, 26.5 mmol) in a mixture of toluene (100 mL) and DMF (2.5 mL, 31.8 mmol) was added oxalyl chloride (3.0 mL, 34 mmol). The mixture was stirred at room temperature for 1 h, and then concentrated to an oil. The oil was dissolved in dichloromethane (100 mL) and cooled to 0 °C in an ice bath. To this solution was added methanol (20 mL) portionwise, maintaining the temperature of the reaction mixture below 10 °C. After 1 h, the mixture was concentrated, and the resulting solid was suspended in diethyl ether and filtered. The solid was triturated with ethyl acetate and diethyl ether and the filtrate was evaporated to provide the title compound as a beige solid.
  • 3
  • [ 69583-00-2 ]
  • [ 6531-04-0 ]
  • [ 1024604-91-8 ]
  • 4
  • [ 124-41-4 ]
  • [ 6531-04-0 ]
  • [ 65202-50-8 ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20℃; for 20h; A solution of 6-chloropyridazine-3-carboxylic acid (0.50 g, 3.2 mmol) in 11 mL of SOCl2 was heated at 75° C. for 2 h and was then concentrated and redissolved in 5 mL of MeOH. To the solution was added a 25percent solution of sodium methoxide (0.75 mL, 3.5 mmol, 1.1 eq) in MeOH. The reaction mixture was stirred at room temperature for 20 h and was then quenched with H2O and extracted with dichloromethane. Silica gel flash chromatography (EtOAc/MeOH 90:10) of the residue afford a 2:1 mixture of the 6-chloropyridazine-3-carboxylic acid and 6-methoxypyridazine-3-carboxylic acid (0.160 g). To a solution of the mixture of ester and chloride in 1.9 mL of p-dioxane was added 4-hydroxy piperidine (0.094 g, 93 mmol) followed by diisopropylethylamine (0.49 mL, 2.8 mmol). The mixture was heated at 100° C. for 20 h then concentrated. Purification with silica gel flash chromatography afforded methyl 6-(4-hydroxypiperidin-1-yl)pyridazine-3-carboxylate (0.15 g, 63 mmol).
 

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