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[ CAS No. 518990-36-8 ] {[proInfo.proName]}

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Chemical Structure| 518990-36-8
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Product Details of [ 518990-36-8 ]

CAS No. :518990-36-8 MDL No. :MFCD03840714
Formula : C9H8N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :NRJPGEXONZLCQP-UHFFFAOYSA-N
M.W : 192.17 Pubchem ID :22477658
Synonyms :

Calculated chemistry of [ 518990-36-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 49.55
TPSA : 75.21 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) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.93
Log Po/w (XLOGP3) : 1.38
Log Po/w (WLOGP) : 1.27
Log Po/w (MLOGP) : 0.48
Log Po/w (SILICOS-IT) : 1.35
Consensus Log Po/w : 1.08

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 : 1.09 mg/ml ; 0.00569 mol/l
Class : Soluble
Log S (Ali) : -2.56
Solubility : 0.526 mg/ml ; 0.00274 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.42
Solubility : 0.739 mg/ml ; 0.00385 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.6

Safety of [ 518990-36-8 ]

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

Application In Synthesis of [ 518990-36-8 ]

* 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 [ 518990-36-8 ]

[ 518990-36-8 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 518990-36-8 ]
  • [ 518990-05-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-methoxy-1H-indazole-3-carboxylic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Stage #2: With water; ammonium chloride In tetrahydrofuran 3; 3 A mixture of 6-methoxy-1H-indazole-3-carboxylic acid (0.200 g, 1.04 mmol) in THF (15 mL) was stirred for 10 min at 0° C. under N2. LAH was added and the mixture was stirred overnight at room temperature under N2. Then, an aqueous NH4Cl solution (5 mL) was added and the reaction mixture was concentrated to half its volume and extracted with EtOAc. The organic layer was washed with brine and water, dried over anhydrous MgSO4, and the solvent removed in vacuo to give a residue. MnO2 (0.680 g, 7.8 mmol) was added to the residue in anhydrous CH2Cl2 (15 mL) at 0° C. with stirring. After the addition, the mixture was stirred at room temperature for 8 h. The mixture was diluted with anhydrous ether (50 mL) and filtered through a pad of Celite. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography to give 6-methoxy-1H-indazole-3-carbaldehyde (0.100 g, 56%).
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;
  • 2
  • [ 518990-36-8 ]
  • [ 64-17-5 ]
  • [ 858671-77-9 ]
YieldReaction ConditionsOperation in experiment
86% With acetyl chloride for 16h; Heating / reflux; 12 Procedure 12 Procedure 12 provides a method for the preparation of N(1)-difluoromethylindazole acids from the corresponding indazole-3-carboxylic acids. Acetyl chloride (141 mmol) was added dropwise to a solution of 6-methoxy-3-indazole-carboxylic acid (26.0 mmol) in ethanol (200 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was allowed to cool to rt and was concentrated. The residue was dissolved in ethyl acetate (300 mL) and was washed with aqueous sodium bicarbonate (2*50 mL). The combined aqueous layers were back-extracted with ethyl acetate (2*200 mL). The combined organic layers were washed with brine (50 mL), dried (sodium sulfate), concentrated, and dried under vacuum to afford 4.91 g (86%) of the ester as a solid.
With sulfuric acid 3 The conversion of the substituted isatins to the corresponding indazole-3- carboxylic acids is essentially the same method as described for indazole-3-carboxylic acid: Snyder, H.R., et. al. J. Am. Chem. Soc. 1952, 74, 2009. The substituted isatin (22.1 mmol) was diluted with 1 N sodium hydroxide (24 mL) and was heated at 50 0C for 30 min. The burgundy solution was allowed to cool to rt and was maintained for Ih. The reaction mixture was cooled to 0 0C and was treated with a 0 0C solution of sodium nitrite (22.0 mmol) in water (5.5 mL). This solution was added through a pipet submerged below the surface of a vigorously stirred solution of sulfuric acid (2.3 mL) in water (45 mL) at 0 0C. The addition took 15 min and the reaction was maintained for an additional 30 min. A cold (0 0C) solution of tin (II) chloride dihydrate (52.7 mmol) in concentrated hydrochloric acid (20 mL) was added to the reaction mixture over 10 min and the reaction mixture was maintained for 60 min. The precipitated solids were isolated by filtration, washed with water, and dried to give a quantitative mass balance. This material was of sufficient purity (1H NMR and LC/MS) to use in the next step without further purification. Alternatively, the acid was recrystallized from acetic acid to provide pure material. Ethyl esters were prepared from the acids using sulfuric acid in ethanol.
  • 3
  • [ 52351-75-4 ]
  • [ 518990-36-8 ]
YieldReaction ConditionsOperation in experiment
100% The conversion of the substituted isatins to the corresponding indazole-3- carboxylic acids is essentially the same method as described for indazole-3-carboxylic acid: Snyder, H.R., et. al. J. Am. Chem. Soc. 1952, 74, 2009. The substituted isatin (22.1 mmol) was diluted with 1 N sodium hydroxide (24 mL) and was heated at 50 0C for 30 min. The burgundy solution was allowed to cool to rt and was maintained for Ih. The reaction mixture was cooled to 0 0C and was treated with a 0 0C solution of sodium nitrite (22.0 mmol) in water (5.5 mL). This solution was added through a pipet submerged below the surface of a vigorously stirred solution of sulfuric acid (2.3 mL) in water (45 mL) at 0 0C. The addition took 15 min and the reaction was maintained for an additional 30 min. A cold (0 0C) solution of tin (II) chloride dihydrate (52.7 mmol) in concentrated hydrochloric acid (20 mL) was added to the reaction mixture over 10 min and the reaction mixture was maintained for 60 min. The precipitated solids were isolated by filtration, washed with water, and dried to give a quantitative mass balance. This material was of sufficient purity (1H NMR and LC/MS) to use in the next step without further purification. Alternatively, the acid was recrystallized from acetic acid to provide pure material. Ethyl esters were prepared from the acids using sulfuric acid in ethanol.
  • 4
  • [ 518990-36-8 ]
  • [ 885520-18-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide In water Reflux; 16 Reference Example 16 6-Hydroxyindazole-3-carboxylic acid 6-Methoxyindazole-3-carboxylic acid (1.015 g; manufactured by Chem Pacific) was dissolved in hydrobromic acid (52 mL; manufactured by Kanto Chemical Co., Inc.), and stirred overnight at reflux. After cooling to room temperature, disppearance of the reacting material and generation of the target compound was confirmed based on LCMS. The solvent was evaporated under reduced pressure to obtain the target compound as a crude product (1.504 g). LCMS: 179.1 [M+H]; retention time: 1.94 minutes: LCMS condition: A
With hydrogen bromide Reflux; 40 Reference Example 40 6-Hydroxyindazole-3-carboxylic acid 6-Methoxyindazole-3-carboxylic acid (1.015 g; manufactured by ChemPacific Corp.) was dissolved in hydrobromic acid (52 mL; manufactured by Kanto Chemical Co., Inc.), and the solution was stirred overnight at reflux. The solution was cooled to room temperature, and then the loss of raw materials and the presence of the title compound were confirmed using LCMS. The solvent was evaporated under reduced pressure, and thus a crude product (1.504 g) of the title compound was obtained.LCMS: 179.1 [M+H]; Retention time: 1.94 minutes; LCMS condition: A
With hydrogen bromide Reflux; 69 6-Hydroxyindazol-3-carboxylic acid 6-Methoxyindazole-3-carboxylic acid (1.015 g; made by Chem. Pacific) was dissolved in hydrobromic acid (52 mL; made by Kanto Chemical Co., Inc.) and [the solution] was stirred overnight under reflux. After [the contents] had been cooled to room temperature, the disappearance of the raw material and the title compound were confirmed using LCMS. The solvent was distilled off under reduced pressure, and a crude product of the title compound (1.504 g) was obtained. LCMS: 179 [M + H]; Retention time: 1.94 min; LCMS conditions: A
1.50 g With hydrogen bromide In water Reflux;

  • 5
  • [ 518990-36-8 ]
  • [ 889134-30-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 2: manganese(IV) oxide / dichloromethane / 24 h / 20 °C / Inert atmosphere 3: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4: manganese(IV) oxide / dichloromethane / 24 h / 20 °C / Inert atmosphere
  • 6
  • [ 518990-36-8 ]
  • [ 518987-37-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 2: manganese(IV) oxide / dichloromethane / 24 h / 20 °C / Inert atmosphere
  • 7
  • [ 518990-36-8 ]
  • [ 889134-39-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 2: manganese(IV) oxide / dichloromethane / 24 h / 20 °C / Inert atmosphere 3: tetrahydrofuran / 0 - 20 °C / Inert atmosphere
  • 8
  • [ 461699-81-0 ]
  • [ 518990-36-8 ]
  • [ 1326283-12-8 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃; To 6-methoxy-1 H-indazole-3-carboxylic acid (64 mg, 0.333 mmol) in dichloromethane (10 ml) was added 2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (166 mg, 0.666 mmol), 0-(7- azabenzotriazol-1-yl)1 ,1 ,3,3-tetramethyluronium hexafluorophosphate (190 mg, 0.500 mmol) and N,N- diisopropylethylamine (0.174 ml, 0.999 mmol). The reaction mixture was stirred overnight at room temperature. Then the reaction mixture was concentrated in vacuo and the residue was purified by column chromatograpy (silica gel; dichloromethane / methanol 99/1 ) and thereafter by column chromatograpy (silica gel; heptane / ethyl acetate 2/1 ) to give 6-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)phenyl)-1 H-indazole-3-carboxamide (54 mg).
  • 9
  • [ 858671-77-9 ]
  • [ 518990-36-8 ]
YieldReaction ConditionsOperation in experiment
With water; sodium hydroxide In methanol 66 To ethyl 6-methoxy-1 H-indazole-3-carboxylate (0.415 mmol) in methanol (5 ml) was added 4N sodium hydroxide (aq) (8 mL, 32.0 mmol). After two hours stirring, reaction was still not finished and 6 ml of 4N NaOH was added. Upon completion of the reaction, the methanol was removed by evaporation and the water layer was washed with ethyl acetate. Subsequently the water layer was acidified and extracted with ethyl acetate twice. The latter organic layers were combined, dried (IV^SO^) and concentrated in vacuo to give 6-methoxy-1 H-indazole-3-carboxylic acid (64 mg) as a brown solid.
  • 10
  • [ 518990-36-8 ]
  • [ 1221178-84-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen bromide / Reflux 2: thionyl chloride / 0 - 60 °C
Multi-step reaction with 2 steps 1: hydrogen bromide / water / Reflux 2: thionyl chloride / 0 - 60 °C
  • 11
  • [ 518990-36-8 ]
  • [ 1221178-87-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide / Reflux 2: thionyl chloride / 0 - 60 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
Multi-step reaction with 5 steps 1: hydrogen bromide / water / Reflux 2: thionyl chloride / 0 - 60 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
  • 12
  • [ 518990-36-8 ]
  • [ 1221178-88-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: hydrogen bromide / Reflux 2: thionyl chloride / 0 - 60 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 60 °C
  • 13
  • [ 518990-36-8 ]
  • [ 1221178-89-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: hydrogen bromide / Reflux 2.1: thionyl chloride / 0 - 60 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4.1: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 7.2: 0 °C
  • 14
  • [ 518990-36-8 ]
  • [ 1221178-90-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: hydrogen bromide / Reflux 2.1: thionyl chloride / 0 - 60 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4.1: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 7.2: 0 °C 8.1: manganese(IV) oxide / dichloromethane; tetrahydrofuran / 20 °C
  • 15
  • [ 518990-36-8 ]
  • [ 1221179-61-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1.1: hydrogen bromide / Reflux 2.1: thionyl chloride / 0 - 60 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4.1: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 7.2: 0 °C 8.1: manganese(IV) oxide / dichloromethane; tetrahydrofuran / 20 °C 9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 9.2: 5 h / 20 °C 10.1: toluene-4-sulfonic acid hydrazide; sodium acetate / 1,2-dimethoxyethane; water / 5.5 h / 95 °C 11.1: sodium hydroxide; water / methanol / 40 °C 12.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 0.25 h / 20 °C 12.2: 20 °C 13.1: hydrogenchloride; water / 1,4-dioxane; methanol / 16 h / 50 °C 14.1: triethylamine / dmap / tetrahydrofuran / 20 °C 15.1: hydrogen / 5%-palladium/activated carbon / water; tetrahydrofuran / 20 °C
  • 16
  • [ 518990-36-8 ]
  • [ 1221178-86-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide / Reflux 2: thionyl chloride / 0 - 60 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: hydrogen bromide / water / Reflux 2: thionyl chloride / 0 - 60 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere
  • 17
  • [ 518990-36-8 ]
  • [ 1221178-92-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: hydrogen bromide / Reflux 2.1: thionyl chloride / 0 - 60 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4.1: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 7.2: 0 °C 8.1: manganese(IV) oxide / dichloromethane; tetrahydrofuran / 20 °C 9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 9.2: 5 h / 20 °C 10.1: toluene-4-sulfonic acid hydrazide; sodium acetate / 1,2-dimethoxyethane; water / 5.5 h / 95 °C
  • 18
  • [ 518990-36-8 ]
  • [ 1221178-93-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: hydrogen bromide / Reflux 2.1: thionyl chloride / 0 - 60 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4.1: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 7.2: 0 °C 8.1: manganese(IV) oxide / dichloromethane; tetrahydrofuran / 20 °C 9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 9.2: 5 h / 20 °C 10.1: toluene-4-sulfonic acid hydrazide; sodium acetate / 1,2-dimethoxyethane; water / 5.5 h / 95 °C 11.1: sodium hydroxide; water / methanol / 40 °C
  • 19
  • [ 518990-36-8 ]
  • [ 1221179-59-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: hydrogen bromide / Reflux 2.1: thionyl chloride / 0 - 60 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4.1: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 7.2: 0 °C 8.1: manganese(IV) oxide / dichloromethane; tetrahydrofuran / 20 °C 9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 9.2: 5 h / 20 °C 10.1: toluene-4-sulfonic acid hydrazide; sodium acetate / 1,2-dimethoxyethane; water / 5.5 h / 95 °C 11.1: sodium hydroxide; water / methanol / 40 °C 12.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 0.25 h / 20 °C 12.2: 20 °C 13.1: hydrogenchloride; water / 1,4-dioxane; methanol / 16 h / 50 °C
  • 20
  • [ 518990-36-8 ]
  • [ 1221179-60-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1.1: hydrogen bromide / Reflux 2.1: thionyl chloride / 0 - 60 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4.1: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 7.2: 0 °C 8.1: manganese(IV) oxide / dichloromethane; tetrahydrofuran / 20 °C 9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 9.2: 5 h / 20 °C 10.1: toluene-4-sulfonic acid hydrazide; sodium acetate / 1,2-dimethoxyethane; water / 5.5 h / 95 °C 11.1: sodium hydroxide; water / methanol / 40 °C 12.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 0.25 h / 20 °C 12.2: 20 °C 13.1: hydrogenchloride; water / 1,4-dioxane; methanol / 16 h / 50 °C 14.1: triethylamine / dmap / tetrahydrofuran / 20 °C
  • 21
  • [ 518990-36-8 ]
  • [ 1221178-85-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide / Reflux 2: thionyl chloride / 0 - 60 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
Multi-step reaction with 3 steps 1: hydrogen bromide / water / Reflux 2: thionyl chloride / 0 - 60 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
  • 22
  • [ 518990-36-8 ]
  • [ 1221178-91-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: hydrogen bromide / Reflux 2.1: thionyl chloride / 0 - 60 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4.1: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 7.2: 0 °C 8.1: manganese(IV) oxide / dichloromethane; tetrahydrofuran / 20 °C 9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 9.2: 5 h / 20 °C
  • 23
  • [ 518990-36-8 ]
  • [ 1221178-94-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: hydrogen bromide / Reflux 2.1: thionyl chloride / 0 - 60 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4.1: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 7.2: 0 °C 8.1: manganese(IV) oxide / dichloromethane; tetrahydrofuran / 20 °C 9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 9.2: 5 h / 20 °C 10.1: toluene-4-sulfonic acid hydrazide; sodium acetate / 1,2-dimethoxyethane; water / 5.5 h / 95 °C 11.1: sodium hydroxide; water / methanol / 40 °C 12.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 0.25 h / 20 °C 12.2: 20 °C
  • 24
  • [ 518990-36-8 ]
  • ethyl 6-(2-(tert-butoxycarbonyl-((2R)-2-(3-(tert-butoxycarbonyl(methylsulfonyl)amino)phenyl)-2-triethylsilyloxyethyl)amino)ethoxy)-1-tetrahydropyran-2-yl-indazole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: hydrogen bromide / water / Reflux 2: thionyl chloride / 0 - 60 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0 - 20 °C / Inert atmosphere
  • 25
  • [ 518990-36-8 ]
  • C40H60N4O11SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: hydrogen bromide / water / Reflux 2: thionyl chloride / 0 - 60 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0 - 20 °C / Inert atmosphere 7: sodium hydroxide / tetrahydrofuran; methanol / 5 h / 40 °C
  • 26
  • [ 518990-36-8 ]
  • C40H62N4O10SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: hydrogen bromide / water / Reflux 2: thionyl chloride / 0 - 60 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0 - 20 °C / Inert atmosphere 7: sodium hydroxide / tetrahydrofuran; methanol / 5 h / 40 °C 8: borane-THF / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
  • 27
  • [ 518990-36-8 ]
  • N-(3-((1R)-1-hydroxy-2-(2-((3-(hydroxymethyl)-1H-indazol-6-yl)oxy)ethylamino)ethyl)phenyl)methanesulfonamide dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: hydrogen bromide / water / Reflux 2: thionyl chloride / 0 - 60 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 4: toluene-4-sulfonic acid / toluene / 60 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 6: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0 - 20 °C / Inert atmosphere 7: sodium hydroxide / tetrahydrofuran; methanol / 5 h / 40 °C 8: borane-THF / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 9: hydrogenchloride / ethanol; water / 24 h / 20 °C
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