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[ CAS No. 53180-92-0 ]

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Chemical Structure| 53180-92-0
Chemical Structure| 53180-92-0
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Product Details of [ 53180-92-0 ]

CAS No. :53180-92-0 MDL No. :MFCD11110434
Formula : C4H4ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :129.55 g/mol Pubchem ID :13001063
Synonyms :

Safety of [ 53180-92-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53180-92-0 ]

  • Downstream synthetic route of [ 53180-92-0 ]

[ 53180-92-0 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 68716-47-2 ]
  • [ 53180-92-0 ]
  • 4-amino-5-(3,4-dichlorophenyl)pyridazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 16h;Heating / reflux; To a solution of 4-amino-5-choloropyridizine (1) (3.25 g, 25 mmol) in toluene (100 mL) under argon add tetrakis(triphenylphosphine)palladium(0) (2.9 g. 2.5 mmol), 2M aqueous sodium carbonate (35 mL) (degassed) and a solution of dicholorobenzeneboronic acid (5.3 g, 27 mmol) in ethanol (35 ml) (degassed). Heat the resulting two phase mixture for 16 hours at reflux under argon. Dilute the reaction with ethyl acetate (50 mL) and wash the organic layer with saturated ammonium chloride, dry (Na2SO4) and evaporate to dryness in vacuo. Purify by flash chromatography and isolate the desired product 2 by combining the appropriate fractions and evaporating to dryness.
  • 3
  • [ 53180-92-0 ]
  • [ 179899-07-1 ]
  • [ 1466574-75-3 ]
YieldReaction ConditionsOperation in experiment
37% General procedure: To a solution of 4-bromo-6-chloropyridazin-3-amine (2.5 g, 12.0 mmol, CAS RN 446273-59-2) in 1,2-dimethoxyethane (30 mL) was added 4-fluoro-2-methoxyphenylboronic acid (2.45 g, 14.4 mmol, CAS RN 179899-07-1) and 2M aqueous sodium carbonate solution (10 mL). The reaction mixture was stirred under argon atmosphere for 15 minutes. Pd(II)acetate (135 mg, 600 mumol) and triphenylphosphine (315 mg, 1.2 mmol) was added. The dark red reaction mixture was stirred at 90 C. for 8 hours and then poured on 10% aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL), filtered over dicalite and the layers were separated. The aqueous layer was extracted a second time with ethyl acetate (200 mL). The organic layers were washed with 200 mL brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography on a 120 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100). Light red solid (1.71 g, 56.2%). MS (ESI+): m/z=254.050 ([M+H]+). The title compound was prepared in analogy to example 1, intermediate b, from 5-chloro-pyridazin-4- ylamine (CAS RN 53180-92-0) and 4-fluoro-2-methoxyphe- nylboronic acid (CAS RN 179899-07-fl and using a gradient of n-heptane:ethyl acetate:methanol (100:0:0 to 0:100:0 to 0:50:50) for the chromatographic purification. Light yellow solid (37%). MS (ESIj: m/z=220.089 ([M+H]j.
  • 4
  • [ 53180-92-0 ]
  • [ 899436-71-6 ]
  • 5-(2-methylpyridin-3-yl)pyridazin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 140℃; for 1h; Preparation 9.2: 5-(2-methylpyridin-3-yl)pyridazin-4-amine 7v [00288] A mixture of <strong>[53180-92-0]5-chloropyridazin-4-amine</strong> (50 mg, 0.386 mmol), (2-methyl-3- pyridyl)boronic acid (63.43 mg, 0.463 mmol), palladium triphenylphosphane (22.3 mg, 0.0193 mmol) and a2C03 (386 mu^ of 2M, 0.772 mmol) in dioxane (2 mL) was heated at 140C for lh. The mixture was then cooled to room temperature and partitioned between DCM and water. The organic layer was filtered through a SCX column, eluting with a 2M solution of H3 in MeOH. The eluate was concentrated in vacuo to give the title compound 7v (72 mg, 100% Yield).
  • 5
  • 4-((3,3-difluoropyrrolidin-1-yl)methyl)piperidine [ No CAS ]
  • [ 53180-92-0 ]
  • 5-(4-((3,3-difluoropyrrolidin-1-yl)methyl)piperidin-1-yl)pyridazin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% In 1-methyl-pyrrolidin-2-one; at 170℃; for 7h;Microwave irradiation; Step 3: 5-(4-((3,3-difluoropyrrolidin-l-yl)methyl)piperidin-l-yl)pyridazin-4-amine 7bb [00292] A mixture of <strong>[53180-92-0]5-chloropyridazin-4-amine</strong> (50 mg, 0.3860 mmol), 4-[(3,3- difluoropyrrolidin- 1 -yl)methyl]piperidine (197.1 mg, 0.9650 mmol) in NMP (lOmL) were heated under microwave conditions at 170C for 7 hours. The reaction was passed through a 10 g SCX-2 cartridge and washed with MeOH/DCM mixtures. The product was eluted by washing the cartridge with 2M H3 in MeOH/DCM mixtures. The solvent was removed in vacuo and the residue was purified by column chromatography (ISCO Companion, 12g column, eluting with 0 to 10% MeOH/DCM, loaded in DCM) to give the sub-title product as a beige solid (27 mg, 23% Yield). 'H NMR (500 MHz, DMSO) delta 8.46 (d, 1H), 8.41 (s, 1H), 5.85 (s, 2H), 3.20 (d, 2H), 2.87 (t, 2H), 2.69 (t, 2H), 2.59 (td, 2H), 2.34 (d, 2H), 2.24 (tt, 2H), 1.83 - 1.74 (m, 2H), 1.65 - 1.53 (m, 1H), 1.43 - 1.30 (m, 2H); 19F MR (471 MHz, DMSO) delta -90.81 ; LC-MS ES +: 298.1, ES -: 296.1.
  • 6
  • [ 20744-39-2 ]
  • [ 53180-92-0 ]
YieldReaction ConditionsOperation in experiment
95.1% With N-chloro-succinimide; 2,2'-azobis(isobutyronitrile); In acetonitrile; at 0 - 25℃; 200 mL of acetonitrile was added to a dry 500 mL three-necked reaction flask, and compound 2 (4-aminopyridazine, 19 g, 200 mmol, 1 eq) was added with stirring, and the reaction solution was cooled to 0 C.Then azobisisobutyronitrile (164 mg, 1.0 mmol, 0.005 eq) was added.Take NCS (N-chlorosuccinimide, 29.3g, 220mmol, 1.1eq) dissolved in 100mL acetonitrile, transfer to a constant pressure dropping funnel, at 0 temperature,Slowly drop into the acetonitrile solution of 4-aminopyridazine, the dropwise addition process lasts 1 to 2 hours, pay attention to maintain the temperature at 0 to 5 .After the dropwise addition, the reaction solution was slowly raised to room temperature (25 C), and the reaction was stirred for 4 to 6 hours.After detecting the disappearance of the reaction raw materials by HPLC, the reaction was quenched with 100 mL of saturated ammonium chloride solution and extracted with ethyl acetate.The organic phase was washed three times with saturated sodium carbonate aqueous solution and once with saturated brine, and the organic phase was dried and spin-dried, and then the crude product was recrystallized with a mixed solution of ethyl acetate: methanol = 5: 15-chloro-4-aminopyridazine (24.64g, yield 95.1%).
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