Alternatived Products of [ 928821-18-5 ]
Product Details of [ 928821-18-5 ]
CAS No. : | 928821-18-5 |
MDL No. : | MFCD09026344 |
Formula : |
C10H13N3
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
175.23
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 928821-18-5 ]
Application In Synthesis of [ 928821-18-5 ]
* 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 [ 928821-18-5 ]
- 1
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[ 928821-18-5 ]
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[ 501-53-1 ]
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[ 945928-60-9 ]
Yield | Reaction Conditions | Operation in experiment |
97% |
With pyridine In dichloromethane at 0 - 20℃; |
11.1
Step 1: Preparation of benzyl l-isopropyl-lH-indazol-5-ylcarbamateBenzyl chloroformate (3.59 mL, 0.0251 mol) is added dropwise to a solution of 1- isopropyl-lH-indazol-5-amine (4.00 g, 0.0228 mol) and pyridine (3.70 mL, 0.0457 mol) in dichloromethane (50 mL) at 0 0C. The reaction is allowed to warm to room temperature and stirred overnight. The solvent is evaporated in vacuo, the residue dissolved in dichloromethane and washed with saturated citric acid solution and brine. The organic layers are dried (MgSO4) and concentrated to afford the title compound (6.88 g, 97%); HPLC (SYMMETRY Ci8 3.5 μM, 4.6 x 30 mm column; gradient elution 2%-98% MeCN with 0.1% TFA over 10 min; 2 mL/min rate): retention time = 5.07 min; MS for Ci8Hi9N3Oa m/z 310.4(M+H)+. |
- 2
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[ 928821-18-5 ]
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methyl (2R)-glycidate
[ No CAS ]
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[ 945928-48-3 ]
Yield | Reaction Conditions | Operation in experiment |
39% |
With lithium trifluoromethanesulfonate In acetonitrile at 55℃; |
1.3
Step 3: Preparation of (R)-methyl 2-hydroxy-3-(l-isopropyl-lH-indazol-5- ylamino)propanoate (R)-Methyl oxirane-2-carboxylate (0.875 mL, 0.00999 mol), 1-isopropyl-lH-indazol-5-amine (1.75 g, 0.00999 mol) and lithium trifluoromethanesulfonate (1.56 g, 0.00999 mol) in acetonitrile (20 mL) are stirred and heated at 55 0C overnight. The reaction is diluted with ethyl acetate, washed with water and brine, the organic layer dried (Mg2SO4) and evaporated.The residue is purified by flash chromatography (50% EtOAc/Hexanes) to give the title compound (1.07 g, 39%); HPLC (SYMMETRY C18 3.5 μM, 4.6 x 30 mm column; gradient elution 2%-98% MeCN with 0.1% TFA over 10 min; 2 mL/min rate): retention time = 3.04 min; MS for C14H19N3O3 m/z 278.3(M+H)+. |
- 3
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[ 945928-47-2 ]
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[ 928821-18-5 ]
Yield | Reaction Conditions | Operation in experiment |
99% |
With iron; ammonium chloride In ethanol; water for 0.75h; Heating / reflux; |
1.2
Step 2: Preparation of l-isopropyl-lH-indazol-5-amineIron powder (2.45 g, 0.0439 mol) is added portionwise to a solution of l-isopropyl-5- nitro-lH-indazole (2.25 g, 0.0110 mol) and ammonium chloride (5.86 g, 0.110 mol) in ethanol (100 mL) and water (45 mL) at 80 0C. The mixture is vigorously stirred and heated for 45 minutes, diluted with dichloromethane (250 ml) and filtered. The organic layer is separated, dried (Mg2SO4) and evaporated to afford the title compound (1.92 g, 99%); HPLC (SYMMETRY Ci8 3.5 μM, 4.6 x 30 mm column; gradient elution 2%-98% MeCN with 0.1% TFA over 10 min; 2 mL/min rate): retention time = 2.69 min; MS for C10H13N3 m/z 176.2(M+H)+. |
- 4
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[ 928821-18-5 ]
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1-isopropyl-4,5,6,7-tetrahydro-1H-indazol-5-ylamine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
56% |
With nishimura’s catalyst; hydrogen In methanol at 20℃; for 6h; |
preparation of intermediates 13a-h
General procedure: To a solution of the respective nitro/amino indazole 12a-h (1.0 equiv) in MeOH was added Nishimura’s catalyst.[1] The mixture was hydrogenated (4 bar hydrogen atmosphere) for 6-53h at RT, filtered and concentrated under reduced pressure. The crude product was purified by preparative reverse-phase HPLC. |
Reference:
[1]Gerlach, Kai; Hobson, Scott; Eickmeier, Christian; Groß, Ulrike; Braun, Clemens; Sieger, Peter; Garneau, Michel; Hoerer, Stefan; Heine, Niklas
[Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3227 - 3241]
- 5
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[ 928821-18-5 ]
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[8-(4-fluoro-2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-(1-isopropyl-4,5,6,7-tetrahydro-1H-indazol-5-yl)amine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: hydrogen; nishimura’s catalyst / methanol / 6 h / 20 °C
2: sodium t-butanolate; johnphos; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 80 °C / Inert atmosphere |
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Reference:
[1]Gerlach, Kai; Hobson, Scott; Eickmeier, Christian; Groß, Ulrike; Braun, Clemens; Sieger, Peter; Garneau, Michel; Hoerer, Stefan; Heine, Niklas
[Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3227 - 3241]
- 6
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[ 928821-18-5 ]
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C19H13BrFNOS
[ No CAS ]
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C29H26BrFN4OS
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
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In acetonitrile at 35℃; for 20h; |
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- 7
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[ 928821-18-5 ]
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C18H23NO2
[ No CAS ]
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C28H36N4O2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
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In acetonitrile at 35℃; for 20h; |
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- 8
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[ 928821-18-5 ]
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C20H21NO4
[ No CAS ]
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C30H34N4O4
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
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In acetonitrile at 35℃; for 20h; |
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