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Chemical Structure| 1208084-53-0
Chemical Structure| 1208084-53-0
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Product Details of [ 1208084-53-0 ]

CAS No. :1208084-53-0 MDL No. :MFCD11976872
Formula : C7H4ClN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :KCIGXZXAPJTRTG-UHFFFAOYSA-N
M.W : 197.58 Pubchem ID :56766638
Synonyms :

Calculated chemistry of [ 1208084-53-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.96
TPSA : 67.49 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.08
Log Po/w (XLOGP3) : 1.15
Log Po/w (WLOGP) : 1.08
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : 0.45
Consensus Log Po/w : 0.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.24
Solubility : 1.15 mg/ml ; 0.00581 mol/l
Class : Soluble
Log S (Ali) : -2.16
Solubility : 1.36 mg/ml ; 0.00689 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.71
Solubility : 3.88 mg/ml ; 0.0196 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.03

Safety of [ 1208084-53-0 ]

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 [ 1208084-53-0 ]

* 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 [ 1208084-53-0 ]

[ 1208084-53-0 ] Synthesis Path-Downstream   1~23

  • 1
  • [ CAS Unavailable ]
  • [ 154578-26-4 ]
  • [ 1208084-53-0 ]
YieldReaction ConditionsOperation in experiment
67% With sodium chlorite; sodium dihydrogenphosphate In tetrahydrofuran; water; <i>tert</i>-butyl alcohol at 20℃; 5.6.153.A Part A. 6-chloroimidazo[1.2-blpyridazine-3-carboxylic acid To a solution of 6-chloroimidazo[1,2-b]pyridazine-3-carbaldehyde (1.82 g, 10 mmol), in t-BuOH (90 ml) and 2-methyl-2-butene in THF (30 ml, 2.0 M) was added a solution of sodium chlorite(80%, 9.0 g, 100 mmol) and NaH2P04 (1 g, 8 mmol) in water (45 ml). The mixture was stirred at rtfor overnight, concentrated, diluted with water, acidified to PH = 4, precipitated white solid, filtered togive 6-chloroimidazo[1,2-b]pyridazine-3-carboxylic acid as white solid (1.2 g, 67% yield).). 1H NMR20 (400 MHz, DMSO-d6) 8 ppm 8.29 (d, J=9.60 Hz, 1 H), 8.22 (s, 1 H), 7.50 (d, J=9.60 Hz, 1 H); LRMS(ESI) mje 198.1 [(M + H)+, calcd for C7H5CIN302 198.6].
  • 2
  • [ 1150566-27-0 ]
  • 6-chloroimidazo[1,2-b]pyridazine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 35℃; for 4h; A mixture of compound 36 (600mg, 2.66mmol) and Lithium hydroxide monohydrate (335mg, 7.98mmol) in tetrahydrofuran/water (10 mL/2.5mL) was stirred at 35C for 4h. The solvent was removed in vacuo. The residue was added water (4mL) and adjusted pH to 3-4 with 1mol/L hydrochloric acid upon which precipitate formed. The precipitate was filtered off, washed with water and dried to afford 6-chloroimidazo[1,2-b]pyridazine-3-carboxylic acid 37 as an off-white solid (519mg, 98%).1H NMR (400MHz, DMSO-d6) delta 13.30 (s, 1H), 8.63-8.20 (m, 2H), 7.61 (d, J=9.5Hz, 1H).
96% With hydrogenchloride; In water; at 90℃; for 15h; A solution of ethyl 6-chloroimidazo[l,2-]pyridazine-3-carboxylate (1.79 g, 7.93 mmol) in HC1 (6 N) (25.0 mL, 823 mmol) in pressure vessel was heated at 90 C for 15 h. A white precipitate formed. The mixture was cooled to 0 C and the solid was collected on a Buchner funnel and was washed with water. The solid was dried under vacuum to give 6-chloroimidazo[l,2-£]pyridazine-3-carboxylic acid (1.5 g, 96% yield) as a colorless solid: 1H NMR (400 MHz, DMSO-d6) delta 13.25 (br s, 1 H), 8.37 (s, 1 H), 8.37 (d, J=9.6 Hz, 1 H), 7.61 (d, J=9.6 Hz, 1 H); LCMS (ESI) m/e 198.1 [(M+H)+, calcd for C7H5N302C1 198.0].
91% With water; sodium hydroxide; In methanol; at 25℃; for 4h; A 500 ml one-necked flask was charged with ethyl 6-chloroimidazo [1,2-b] pyridazine-3-carboxylate (11.28 g, 50 mmol)And methanol 50ml,Sodium hydroxide (4.0 g, 100 mmol)Dissolved in 100ml of water,Added to the reaction flask,The reaction was completed at 25 C for 4 hours. The reaction was completed by TLC and neutralized with 30% hydrochloric acid until pH = 4. The mixture was suction filtered, the filter cake was washed with a small amount of water,Dry to give 6-chloroimidazo [1,2-b] pyridazine-3-carboxylic acid purity, yield 91%.
71.4% With water; lithium hydroxide; In tetrahydrofuran; at 30℃; for 3h; Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (0.6 g, 2.66 mmol) was dissolved in tetrahydrofuran/water solution (12 ml/4 ml) and added to hydrated lithium hydroxide at 30C for 3 hours. Concentrate under reduced pressure, add 4ml of water to dissolve, then add 1mol/L dilute hydrochloric acid solution to adjust the pH value to 3, precipitate solids, suction filter, and dry to obtain 0.375g of white solid. Yield: 71.4%.

  • 3
  • [ 1208084-53-0 ]
  • [ 1268454-86-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 0.5 h / 100 °C 2: dichloromethane / 0.17 h / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 1 h / 100 °C
Multi-step reaction with 3 steps 1: thionyl chloride / 0.5 h / 100 °C 2: dichloromethane / 0.17 h / 20 °C 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 1 h / 100 °C
  • 5
  • [ 1208084-53-0 ]
  • [ 1404480-57-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 0.5 h / 100 °C 2: dichloromethane / 0.17 h / 20 °C
Multi-step reaction with 2 steps 1: thionyl chloride / 0.5 h / 100 °C 2: dichloromethane / 0.17 h / 20 °C
  • 6
  • [ 1208084-53-0 ]
  • [ 1154708-13-0 ]
  • [ 1661001-81-5 ]
YieldReaction ConditionsOperation in experiment
1.4 g With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 12h; 11.D Part D. 6-chloro-N-(3-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-b]pyridazine-3-carboxamide To a mixture of 6-chloroimidazo[l,2-]pyridazine-3-carboxylic acid (1.22 g, 6.17 mmol) and 3-(5-isopropyl-l,2,4-oxadiazol-3-yl)aniline (1.882 g, 9.26 mmol) in CH2CI2 (30 mL) at room temperature was added N,N-diisopropylethylamine (5.4 mL, 31 mmol) and HATU (3.52 g, 9.26 mmol). The reaction mixture was stirred at room tmeprature for 12 hours. The mixture was transferred to a separatory funnel containing saturated aqueous NaHC03 solution (50 mL) and was extracted with CH2CI2 (3 x 50 mL). The organic layer was concentrated and the residue was purified by column chromatography on silica gel (30%→ 40% ethyl acetate in hexanes) to afford 6-chloro-N-(3-(5-isopropyl-l,2,4-oxadiazol-3- yl)phenyl)imidazo[l,2-]pyridazine-3-carboxamide (1.4 g, 59% yield) as a yellow solid: 1H NMR (400 MHz, CD3OD) δ 8.40-8.45 (m, 2H), 8.23 (d, J= 9.6 Hz, 1H), 7.78-7.86 (m, 2H), 7.55 (d, J= 9.3 Hz, 1H), 7.50 (t, J= 7.9 Hz, 1H), 3.33 (q, J= 7.1 Hz, 1H), 1.45 (d, J= 7.1 Hz, 6H); LRMS (ESI) mle 383.3 [(M + H)+, calcd for
  • 7
  • [ 1208084-53-0 ]
  • [ 2042167-28-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: potassium carbonate / dimethyl sulfoxide / 12 h / 120 °C
  • 8
  • [ 1208084-53-0 ]
  • [ 2042167-29-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: potassium carbonate / dimethyl sulfoxide / 12 h / 120 °C
  • 9
  • [ 1208084-53-0 ]
  • [ 2042167-31-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: potassium carbonate / dimethyl sulfoxide / 12 h / 120 °C
  • 10
  • [ 1208084-53-0 ]
  • [ 2042167-32-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: potassium carbonate / dimethyl sulfoxide / 12 h / 120 °C
  • 11
  • [ 1208084-53-0 ]
  • [ 2042167-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: potassium carbonate / tetrahydrofuran; dimethyl sulfoxide / 12 h / 120 °C
  • 12
  • [ 1208084-53-0 ]
  • [ 2042170-39-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: potassium carbonate; isopropylamine / dimethyl sulfoxide / 84 h / 20 - 120 °C
  • 13
  • [ 1208084-53-0 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In methanol at 20℃; I89 sodium 6-methoxyimidazo[1,2-b]pyridazine-3-carboxylate A mixture of 6-chloroimidazo[1 ,2-b]pyridazine-3-carboxylic acid (190 mg, 962 pmol, GAS No.1208084-53-0) and sodium methanolate (660 p1, 25 % in methanol , 2.9 mmol) in methanol(2.9 ml) was stirred at room temperature over night. The precipitate was collected byfiltration, washed with methanol and dried to give a mixture of product and starting material.The mixture was resubmitted to similar reaction conditions to give the title compound asmixture with the starting material (185 mg, 3:1 by 1 H NMR) which was used in the next stepwithout further purification.LG-MS (Method 1): R = 0.49 mm; MS (ESIpos) m/z = 194.1 [M+H].1HNMR (400 MHz, DMSO-d6): ö [ppm] = 7.90 (dd, 1H), 7.69-7.59 (m, 1H), 6.78 (dd, 1H),3.93 (5, 3H).
  • 14
  • [ 1208084-53-0 ]
  • [ 2042170-55-6 ]
  • [ 2042167-27-9 ]
YieldReaction ConditionsOperation in experiment
60% With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; 47 6-chloro-N-{trans-4-[(2-chloro-4-fluorophenyl)carbamoyl]cyclohexyl }i midazo[1 ,2- b]pyridazine-3-carboxamide (benzotriazol-1 -yloxy)tripyrrolidinophosphonium hexafluorophosphate (1 .17 g, 3.30 mmol)was added to a mixture of 6-chloroimidazo[1 ,2-b]pyridazine-3-carboxylic acid (593 mg, 3.00mmol, GAS No. 1208084-53-0), trans-4-am ino-N-(2-chloro-4-fluorophenyl)cyclohexanecarboxamide hydrochloride (307 mg, 3.30 mmol) and N-ethyl-Nisopropylpropan-2-amine (2.6 ml, 15 mmol) in 33 ml N,N-dimethylformamide and the mixture was stirred over night at room temperature. For work-up, the reaction mixuture was concentrated under reduced pressure and the residue was stirred with a mixture of water and methanol. The precipitate was collected by filtration, washed with water and methanol anddried to yield the title compound (815 mg, 60% yield).LG-MS (Method 1): R = 1 .09 mm; MS (ESIpos) m/z = 550.2 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 9.50 (br. s, 1H), 8.40 (d, 1H), 8.30 (5, 1H), 8.27-8.21 (m, 1H), 7.65-7.57 (m, 2H), 7.51 (dd, 1H), 7.23 (td, 1H), 3.90-3.76 (m, 1H), 2.14-2.02 (m, 2H), 2.02-1.92 (m, 2H), 1.67-1.51 (m, 2H), 1.49-1.35 (m, 2H).
  • 15
  • [ 1208084-53-0 ]
  • [ 2127172-95-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C / Inert atmosphere
  • 16
  • [ 1208084-53-0 ]
  • [ 2127172-96-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / dichloromethane; tetrahydrofuran / 1 h / 20 °C
  • 17
  • [ 1208084-53-0 ]
  • [ 2127172-79-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / dichloromethane; tetrahydrofuran / 1 h / 20 °C 4: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
  • 18
  • [ 1208084-53-0 ]
  • [ 1831151-12-2 ]
  • [ 2127172-94-3 ]
YieldReaction ConditionsOperation in experiment
20% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; 3 Example 3 (0298) (0299) N-[3-[5-chloro-2-(difluoromethoxy)phenyl]- lH-pyrazol-4-yl]-6-ethynyl-imidazo[l,2- b]pyridazine-3-carboxamide Example 3 (0298) (0299) N-[3-[5-chloro-2-(difluoromethoxy)phenyl]- lH-pyrazol-4-yl]-6-ethynyl-imidazo[l,2- b]pyridazine-3-carboxamide - - (0300) (0301) To a solution of 6-chloroimidazo[l,2-b]pyridazine-3-carboxylic acid (500 mg, 2.53 mmol) in DMF (10 ml) was added HATU (1060 mg, 2.78 mmol), DIPEA (1330 mg, 10.1 mmol ) and 5-[5-chloro-2-(difluoromethoxy)phenyl]-l- (2- trimethylsilylethoxymethyl)pyrazol-4-amine (987 mg, 2.53 mmol). The resulting solution was stirred for 1 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with heptane/ethyl acetate (100/0-0/100) to give 17 mg (20%) of 6-chloro-N-[5-[5-chloro-2- (difluoromethoxy)phenyl]-l-(2-trimethylsilylethoxymethyl)pyrazol-4-yl]imidazo[l,2- b]pyridazine-3-carboxamide as a solid. LC/MS (Method J, ESI): [M+H]+ = 569.0, RT= 1.65 min;
  • 19
  • [ 1201935-84-3 ]
  • 6-chloroimidazo[1,2-b]pyridazine-3-carboxylic acid [ No CAS ]
  • 6-chloro-N-(3-cyano-1-methyl-1H-pyrazole 4-yl)imidazo[1,2-b]pyridazine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.4% With 2-(7-oxybenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 2h; 6-chloroimidazo[1,2-b]pyridazine-3-carboxylic acid (0.35 g, 1.77 mmol) and <strong>[1201935-84-3]4-amino-1-methyl-1H-pyrazole-3-carbonitrile</strong> (0.197 g, 1.61 mmol) was dissolved in 10 ml of acetonitrile, HATU (1.22 g, 3.22 mmol) and DIPEA (0.52 g, 4.03 mmol) were added and the mixture was reacted at room temperature for 2 hours. Water (30 ml) was added to precipitate a solid which was filtered off with suction and dried in the infrared to give 0.41 g of a white solid. Yield: 84.4%.
  • 20
  • [ 1208084-53-0 ]
  • [ 2183503-70-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2-(7-oxybenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 2 h / 20 °C 2: potassium fluoride / dimethyl sulfoxide / 5 h / 100 °C
  • 21
  • [ 1151801-37-4 ]
  • [ 1208084-53-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetonitrile / 3 h / Reflux 1.2: 3 h / 20 °C 2.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 30 °C
Multi-step reaction with 2 steps 1.1: acetonitrile / 3 h / 80 °C 1.2: 3 h / 20 °C 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 4 h / 35 °C
  • 23
  • [ 1208084-53-0 ]
  • [ 1801762-09-3 ]
  • [ 2411566-95-3 ]
YieldReaction ConditionsOperation in experiment
67% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; A solution of compound 37 (300mg, 1.52mmol), 3-(difluoromethyl)-1-methyl-1H-pyrazol-4-amine 25 (203mg, 1.38mmol), EDCI (317mg, 1.66mmol), HOBT (223mg, 1.66mmol) and N,N-diisopropylethylamine (570μL, 3.45mmol) in DMF (10mL) was stirred overnight at room temperature. The reaction was taken up in ethyl acetate (50mL), and the organics were washed with water and brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography eluting with 1% MeOH in DCM to afford compound 38 as a white solid (303mg, 67%). 1H NMR (300MHz, DMSO-d6) δ 8.47 (s, 1H), 7.57 (d, J=9.1Hz, 1H), 7.14 (d, J=9.1Hz, 1H), 3.12 (s, 3H), 3.01 (s, 3H). MS (ESI): 349.2 [M+Na]+.
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