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[ CAS No. 123531-27-1 ] {[proInfo.proName]}

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Chemical Structure| 123531-27-1
Chemical Structure| 123531-27-1
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Quality Control of [ 123531-27-1 ]

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Product Details of [ 123531-27-1 ]

CAS No. :123531-27-1 MDL No. :MFCD17016047
Formula : C9H9N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RJOLUKGMRJYPRZ-UHFFFAOYSA-N
M.W : 191.19 Pubchem ID :10821535
Synonyms :

Calculated chemistry of [ 123531-27-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.07
TPSA : 56.49 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 0.88
Log Po/w (WLOGP) : 0.91
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : 0.57
Consensus Log Po/w : 1.07

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.86
Solubility : 2.65 mg/ml ; 0.0139 mol/l
Class : Very soluble
Log S (Ali) : -1.65
Solubility : 4.27 mg/ml ; 0.0224 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.2
Solubility : 1.21 mg/ml ; 0.00635 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 123531-27-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 123531-27-1 ]

* 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 [ 123531-27-1 ]

[ 123531-27-1 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 5469-70-5 ]
  • [ 70-23-5 ]
  • [ 123531-27-1 ]
YieldReaction ConditionsOperation in experiment
20% In ethanol for 16h; Reflux; 1.1 Step I. Synthesis of ethyl imidazo[I, 2-b]pyridazine-2-carboxylate (Cl). A mixture of pyridazin-3-amine (20 g, 210 mmol) and ethyl 3-bromo-2-oxopropanoate(82 g, 420 mmol) in ethanol (300 mL) was heated at reflux for 16 hours. After removalof solvent via distillation, the residue was taken up in 2 M hydrochloric acid (100 mL)and washed with ethyl acetate. The aqueous layer was basified to a pH ofapproximately 8 via addition of aqueous sodium bicarbonate solution and thenextracted with chloroform; this organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Eluent: 20% ethyl acetate in petroleum ether) afforded the product as a brown solid. Yield: 8.0 g, 42 mmol, 20%. LCMS m/z 192.0 [M+H]. 1H NMR (400 MHz, CDCI3) ö 8.53 (5, 1H), 8.39 (dd, J=4.4, 1.6Hz, 1H), 8.01 -8.04 (m, 1H), 7.12 (dd, J=9.3, 4.4 Hz, 1H), 4.48 (q, J=7.1 Hz, 2H), 1.45 (t, J=7.1 Hz, 3H).
20% In ethanol for 16h; Inert atmosphere; Reflux;
13% In ethanol Heating;
  • 2
  • [ 123531-27-1 ]
  • [ 123531-29-3 ]
YieldReaction ConditionsOperation in experiment
62% With ammonium hydroxide In methanol for 4h; Ambient temperature;
  • 3
  • [ 123531-27-1 ]
  • imidazo[1,2-b]pyridazine-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With hydrogenchloride for 3h; Heating;
  • 4
  • [ 123531-27-1 ]
  • [ 104197-14-0 ]
  • ethyl 3-(3,5-difluoro-4-methoxyphenyl)imidazo[1,2-b]-pyridazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With tetrakis(triphenylphosphine) palladium(0); palladium diacetate; potassium carbonate; In N,N-dimethyl-formamide; at 110℃;Inert atmosphere; A mixture of Cl (500 mg, 2.6 mmol), 5-bromo-1 ,3-difluoro-2-methoxybenzene (864 mg,3.87 mmol), and potassium carbonate (866 mg, 6.27 mmol) in N,N-dimethylformamide(10 mL) was degassed with nitrogen several times. Palladium(II) acetate (50 mg, 0.22 mmol) and tetrakis(triphenylphosphine)palladium(0) (30 mg, 26 pmol) were added, and the reaction mixture was stirred at 110 C overnight. After addition of water (50 mL), the mixture was extracted with ethyl acetate (3 x 30 mL); the combined organic layers wereconcentrated in vacuo and purified by chromatography on silica gel to provide the product as a yellow solid. Yield: 500 mg, 1.5 mmol, 58%. LCMS m/z 334.0 [M+H].
  • 5
  • [ 123531-27-1 ]
  • ethyl 3-(4-chlorophenyl)imidazo[1,2-b]pyridazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-iodo-succinimide / acetonitrile / 72 h / 20 °C 2: sodium carbonate; [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloro palladium(II) / water; 1,4-dioxane / 90 °C
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / dichloromethane / 0 - 25 °C / Inert atmosphere 2: cesium fluoride; bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II) / 1,4-dioxane; water / 100 °C / Inert atmosphere
  • 6
  • [ 123531-27-1 ]
  • 3-(4-chlorophenyl)imidazo[1,2-b]pyridazine-2-carboxylic acid sodium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-iodo-succinimide / acetonitrile / 72 h / 20 °C 2: sodium carbonate; [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloro palladium(II) / water; 1,4-dioxane / 90 °C 3: sodium hydroxide; water / methanol; tetrahydrofuran / 4 h / 20 °C
  • 7
  • [ 123531-27-1 ]
  • azetidin-1-yl[3-(4-chlorophenyl)imidazo[1,2-b]pyridazin-2-yl]methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-iodo-succinimide / acetonitrile / 72 h / 20 °C 2.1: sodium carbonate; [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloro palladium(II) / water; 1,4-dioxane / 90 °C 3.1: sodium hydroxide; water / methanol; tetrahydrofuran / 4 h / 20 °C 4.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.03 h 4.2: 50 °C
  • 8
  • [ 123531-27-1 ]
  • 3-(3,5-difluoro-4-methoxyphenyl)imidazo[1,2-b]pyridazine-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; palladium diacetate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 110 °C / Inert atmosphere 2: lithium hydroxide; water / ethanol / 4 h / 20 °C
Multi-step reaction with 2 steps 1: potassium carbonate; palladium diacetate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 110 °C / Inert atmosphere 2: lithium hydroxide / water; ethanol / 4 h / 25 °C / Inert atmosphere
  • 9
  • [ 123531-27-1 ]
  • azetidin-1-yl[3-(3,5-difluoro-4-methoxyphenyl)imidazo[1,2-b]pyridazin-2-yl]methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; palladium diacetate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 110 °C / Inert atmosphere 2: lithium hydroxide; water / ethanol / 4 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C
Multi-step reaction with 3 steps 1: potassium carbonate; palladium diacetate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 110 °C / Inert atmosphere 2: lithium hydroxide / water; ethanol / 4 h / 25 °C / Inert atmosphere 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 25 °C / Inert atmosphere
  • 10
  • [ 123531-27-1 ]
  • N-cyclopropyl-3-(2-methoxypyrimidin-5-yl)imidazo[1,2-b]pyridazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-iodo-succinimide / acetonitrile / 72 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 110 °C / Inert atmosphere 3: calcium chloride / methanol / 5 h / 50 °C
  • 11
  • [ 123531-27-1 ]
  • ethyl 3-(2-methoxypyrimidin-5-yl)imidazo[1,2-b]pyridazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-iodo-succinimide / acetonitrile / 72 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 110 °C / Inert atmosphere
  • 12
  • [ 123531-27-1 ]
  • ethyl 3-bromoimidazo[1,2-b]pyridazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With N-Bromosuccinimide In dichloromethane at 0 - 20℃; 5.1 Step 1. Synthesis of ethyl 3-bromoimidazo[1, 2-b]pyridazine-2-carboxylate (C8). N-Bromosuccinimide (25.6 g, 144 mmol) was added to a 0 °C solution of Cl (25.0 g,131 mmol) in dichloromethane (250 mL). The reaction mixture was allowed to gradually warm to room temperature and stir overnight, whereupon the reaction was quenched with 10% aqueous sodium bisulfite solution. The resulting mixture was diluted with additional dichloromethane and washed with saturated aqueous sodium bicarbonate solution and with water. The organic layer was dried over magnesium sulfate, filtered,and concentrated in vacuo. Trituration with tert-butyl methyl ether afforded the product as a pinkish-mauve solid (25.4 g). Concentration of the filtrate under reduced pressure was followed by trituration with tert-butyl methyl ether and hexanes to give a second batch of product (6.46 g). Combined yield: 31.9 g, 118 mmol, 90%. LCMS m/z 270.0, 272.0 [M+H]. 1H NMR (400 MHz, CDCI3) ö 8.55 (dd, J=4.4, 1.6 Hz, 1H), 8.05 (dd,J=9.3, 1.6 Hz, 1H), 7.22 (dd, J=9.3, 4.4 Hz, 1H), 4.53 (q, J=7.l Hz, 2H), 1.49 (t, J=7.1 Hz, 3H).
90% With N-Bromosuccinimide In dichloromethane at 0 - 25℃; Inert atmosphere;
  • 13
  • [ 123531-27-1 ]
  • 3-bromo-N-cyclopropylimidazo[1,2-b]pyridazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / dichloromethane / 0 - 20 °C 2: calcium chloride / methanol / 72 h / 50 °C
  • 14
  • [ 123531-27-1 ]
  • 3-(6-cyanopyridin-3-yl)-N-cyclopropylimidazo[1,2-b]pyridazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / dichloromethane / 0 - 20 °C 2.1: calcium chloride / methanol / 72 h / 50 °C 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; 2-methyltetrahydrofuran / 0.03 h / 80 °C / Inert atmosphere 3.2: 80 °C
  • 15
  • [ 123531-27-1 ]
  • N-cyclopropyl-3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)imidazo[1,2-b]pyridazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / dichloromethane / 0 - 20 °C 2: calcium chloride / methanol / 72 h / 50 °C 3: sodium carbonate; [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloro palladium(II) / water; 1,4-dioxane / 20 h / 100 °C
  • 16
  • [ 123531-27-1 ]
  • ethyl 3-(4-chloro-3-fluorophenyl)imidazo[1,2-b]pyridazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-iodo-succinimide / acetonitrile / 72 h / 20 °C 2: sodium carbonate; [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloro palladium(II) / water; 1,4-dioxane / 85 °C
  • 17
  • [ 123531-27-1 ]
  • 3-(4-chloro-3-fluorophenyl)imidazo[1,2-b]pyridazine-2-carboxylic acid lithium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-iodo-succinimide / acetonitrile / 72 h / 20 °C 2: sodium carbonate; [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloro palladium(II) / water; 1,4-dioxane / 85 °C 3: lithium hydroxide monohydrate; water / methanol / 16 h / 20 °C
  • 18
  • [ 123531-27-1 ]
  • 3-(4-chloro-3-fluorophenyl)-N-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-iodo-succinimide / acetonitrile / 72 h / 20 °C 2.1: sodium carbonate; [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloro palladium(II) / water; 1,4-dioxane / 85 °C 3.1: lithium hydroxide monohydrate; water / methanol / 16 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C 4.2: 2 h / 35 °C
  • 19
  • [ 123531-27-1 ]
  • azetidin-1-yl(3-bromoimidazo[1,2-b]pyridazin-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / dichloromethane / 0 - 20 °C 2.1: triethylamine / methanol / 0.17 h / 20 °C 2.2: 50 °C
  • 20
  • [ 123531-27-1 ]
  • azetidin-1-yl[3-(pyrazolo[1,5-a]pyridin-6-yl)imidazo[1,2-b]pyridazin-2-yl]methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / dichloromethane / 0 - 20 °C 2.1: triethylamine / methanol / 0.17 h / 20 °C 2.2: 50 °C 3.1: bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II); cesium fluoride / water; toluene; 1,2-dichloro-ethane / 23 h / 100 °C / Inert atmosphere
  • 21
  • [ 123531-27-1 ]
  • 3-(4-chloro-2,5-difluorophenyl)-N-cyclopropylimidazo[1,2-b]pyridazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / dichloromethane / 0 - 20 °C 2: calcium chloride / methanol / 72 h / 50 °C 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; 2-methyltetrahydrofuran / 80 °C / Inert atmosphere
  • 22
  • [ 123531-27-1 ]
  • ethyl 3-iodoimidazo[1,2-b]pyridazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With N-iodo-succinimide In acetonitrile at 20℃; for 72h; 1.2 Step 2. Synthesis of ethyl 3-iodoimidazo[1, 2-b]pyridazine-2-carboxylate (C2). N-Iodosuccinimide (24.6 g, 109 mmcl) was added to a solution of Cl (19 g, 99 mmcl) in acetonitrile (250 mL), and the reaction mixture was stirred at room temperature for 24hours. Additional N-iodosuccinimide (1 equivalent after every 24 hours) was introduced and stirring continued for a further 48 hours (72 hours overall), until complete consumption of starting material was indicated via thin layer chromatographic analysis. After removal of solvent in vacuo, the residue was taken up in dichloromethane and washed with 1 M hydrochloric acid and with water. The organic layer was dried oversodium sulfate, filtered, and concentrated under reduced pressure; silica gel chromatography (Eluent: 20% ethyl acetate in petroleum ether) provided the product as an off-white solid. Yield: 14.5 g, 45.7 mmol, 46%. LCMS m/z 318.0 [M+H]. 1H NMR (300 MHz, DMSO-d6) ö 8.74 (dd, J=4.3, 1.3 Hz, 1H), 8.18 (dd, J=9.2, 1.4 Hz, 1H), 7.41 (dd, J=9.3, 4.4 Hz, 1H), 4.35 (q, J=7.0 Hz, 2H), 1.36 (t, J=7.1 Hz, 3H).
  • 23
  • [ 123531-27-1 ]
  • 4-[2-(azetidin-1-ylcarbonyl)imidazo[1,2-b]pyridazin-3-yl]-2-fluorobenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / dichloromethane / 0 - 20 °C 2.1: triethylamine / methanol / 0.17 h / 20 °C 2.2: 50 °C 3.1: (bis(tricyclohexyl)phosphine)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 20 h / 100 °C
  • 24
  • [ 70-23-5 ]
  • [ 123531-27-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / Reflux 2: hydrogen; palladium 10% on activated carbon / methanol / 2 h / 20 °C
  • 25
  • [ 64067-99-8 ]
  • [ 123531-27-1 ]
YieldReaction ConditionsOperation in experiment
93% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 2h; 6-chloro - imidazo [l, 2-b] pyridazine-2-carboxylate (8.2 g, 36 mmol)was dissolved in methanol (250 mL), and under nitrogen to which was added 10%palladium on carbon catalyst (lg ), then the system was replaced with hydrogenthree times, the reaction was continued at room temperature for 2h. Aftercompletion of the reaction by TLC, the catalyst was removed by filtration, thefilter cake washed with methanol. The filtrate was concentrated underreduced pressure, to give an intermediate without further purification imidazo[l, 2-b] pyridazine-2-carboxylate (yellow solid, 6.4 g), yield 93%.
  • 26
  • [ 123531-27-1 ]
  • imidazo[1,2-b]pyridazin-2-ylmethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.7 g With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4h; 10.3 The third step: imidazo [l, 2-b] pyridazin-2-yl - methanol Thelithium aluminiumhydride (3.8 g, 100 mmol) in 250 mL nitrogen into a three-necked flask, underice-cooling and thereto was slowly injected anhydrous tetrahydrofuran (100 mL),until no bubbles, thereto was slowly added imidazo [l, 2-b]pyridazine-2-carboxylate (6.4 g, 33.5 mmol), at room temperature the reaction4h. After completion of the reaction is detected by thin layer chromatography,the reaction solution was cooled with an ice bath to 0 C,thereto was slowly added dropwise water (3.8 mL) and 10% sodium hydroxidesolution (3.8 mL), stirred for half an hour. Filtered under reducedpressure, the filter cake was washed several times with ethyl acetate, and thefiltrate concentrated under reduced pressure, and the residue was purified bysilica gel column chromatography to give the intermediate imidazo [l, 2-b]pyridazin-2-yl - methanol (yellow solid, 2.7 g).
  • 27
  • [ 123531-27-1 ]
  • imidazo[1,2-b]pyridazine-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C 2: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2 h / 20 °C / Cooling with ice
  • 28
  • [ 123531-27-1 ]
  • 2-(difluoromethyl)imidazo[1,2-b]pyridazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C 2: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2 h / 20 °C / Cooling with ice 3: diethylamino-sulfur trifluoride / dichloromethane / 0 - 20 °C
  • 29
  • [ 123531-27-1 ]
  • azetidin-1-yl[3-(3,5-difluoro-4-hydroxyphenyl)imidazo[1,2-b]-pyridazin-2-yl]methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; palladium diacetate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 110 °C / Inert atmosphere 2: lithium hydroxide / water; ethanol / 4 h / 25 °C / Inert atmosphere 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 25 °C / Inert atmosphere 4: boron tribromide / dichloromethane / 16 h / 0 - 25 °C / Inert atmosphere
  • 30
  • [ 123531-27-1 ]
  • 3-(4-chlorophenyl)-N-cyclopropyl-N-methyl-imidazo[1,2-b]-pyridazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / dichloromethane / 0 - 25 °C / Inert atmosphere 2: cesium fluoride; bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II) / 1,4-dioxane; water / 100 °C / Inert atmosphere 3: sodium hydroxide / water; methanol / 3 h / 60 °C / Inert atmosphere 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 25 °C / Inert atmosphere
  • 31
  • [ 123531-27-1 ]
  • 3-(4-chlorophenyl)imidazo[1,2-b]pyridazine-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / dichloromethane / 0 - 25 °C / Inert atmosphere 2: cesium fluoride; bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II) / 1,4-dioxane; water / 100 °C / Inert atmosphere 3: sodium hydroxide / water; methanol / 3 h / 60 °C / Inert atmosphere
  • 32
  • [ 123531-27-1 ]
  • 3-(4-chlorophenyl)-N-cyclopropyl-imidazo[1,2-b]pyridazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide / dichloromethane / 0 - 25 °C / Inert atmosphere 2.1: cesium fluoride; bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II) / 1,4-dioxane; water / 100 °C / Inert atmosphere 3.1: sodium hydroxide / water; methanol / 3 h / 60 °C / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere
  • 33
  • [ 123531-27-1 ]
  • azetidin-1-yl[3-(3,5-difluoro-4-[3-3H]methoxyphenyl)imidazo[1,2-b]pyridazin-2-yl]methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate; palladium diacetate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 110 °C / Inert atmosphere 2: lithium hydroxide / water; ethanol / 4 h / 25 °C / Inert atmosphere 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 25 °C / Inert atmosphere 4: boron tribromide / dichloromethane / 16 h / 0 - 25 °C / Inert atmosphere 5: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 °C / Inert atmosphere
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Chemical Structure| 1187236-98-1

[ 1187236-98-1 ]

Ethyl 6-bromoimidazo[1,2-b]pyridazine-2-carboxylate

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Chemical Structure| 1416438-64-6

[ 1416438-64-6 ]

Ethyl 6-methylimidazo[1,2-b]pyridazine-2-carboxylate

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Chemical Structure| 1420623-75-1

[ 1420623-75-1 ]

Ethyl imidazo[1,2-b]pyridazine-3-carboxylate

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Related Parent Nucleus of
[ 123531-27-1 ]

Other Aromatic Heterocycles

Chemical Structure| 1416438-64-6

[ 1416438-64-6 ]

Ethyl 6-methylimidazo[1,2-b]pyridazine-2-carboxylate

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Chemical Structure| 1420623-75-1

[ 1420623-75-1 ]

Ethyl imidazo[1,2-b]pyridazine-3-carboxylate

Similarity: 0.93

Chemical Structure| 1187236-98-1

[ 1187236-98-1 ]

Ethyl 6-bromoimidazo[1,2-b]pyridazine-2-carboxylate

Similarity: 0.90

Chemical Structure| 1416438-64-6

[ 1416438-64-6 ]

Ethyl 6-methylimidazo[1,2-b]pyridazine-2-carboxylate

Similarity: 0.93

Chemical Structure| 1420623-75-1

[ 1420623-75-1 ]

Ethyl imidazo[1,2-b]pyridazine-3-carboxylate

Similarity: 0.93