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Product Details of [ 1201935-85-4 ]

CAS No. :1201935-85-4 MDL No. :MFCD25371334
Formula : C5H7N3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :PQCDQLCMCVXEHN-UHFFFAOYSA-N
M.W : 157.13 Pubchem ID :67308922
Synonyms :

Safety of [ 1201935-85-4 ]

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 [ 1201935-85-4 ]

* 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 [ 1201935-85-4 ]

[ 1201935-85-4 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 400755-41-1 ]
  • [ 74-88-4 ]
  • [ 1201935-85-4 ]
YieldReaction ConditionsOperation in experiment
Potassium carbonate (4.42 g) was added to a solution of 3-methoxy-4-nitro-lH- pyrazole (3.05 g) in DMF (35 ml) and the reaction mixture stirred at room temperature for 5 minutes. Methyl iodide (6.6 ml) was added slowly and the solution stirred for a further 3 hours at room temperature. The reaction mixture was poured into water (50 ml) and the aqueous phase extracted with EtOAc (4 x 50ml). The combined organic extracts were washed with water (50 ml), brine (50 ml) and dried (magnesium sulfate). The solvent was removed in vacuo to give 3-methoxy-l-methyl-4-nitropyrazole as a pale yellow solid (3.9Og, containing -20% wt DMF).
  • 2
  • [ 1201935-85-4 ]
  • [ 332069-74-6 ]
YieldReaction ConditionsOperation in experiment
91% With palladium on activated charcoal; hydrogen In methanol at 25℃; for 4h; 17.17-3 Example 17-3: 3-Methoxy-1-methyl-1H-pyrazol-4-amine Compound 17-2 (8.9 g, 57 mmol) was dissolved in methanol (50 mL). After Pd/C (0.9 g) was added under hydrogen atmosphere, the reaction solution was stirred at 25°C for 4 hours. After the reaction was completed, monitored by LCMS, then the reaction solution was filtered. The obtained filtrate was evaporated under reduced pressure to afford a dark red liquid 17-3 (6.6 g, 91%). ESI-MS m/z=128[M+H] +. 1H NMR (400 MHz, DMSO) δ 6.90 (s, 1H), 3.74 (s, 3H), 3.52 (s, 3H), 3.31 (s, 2H).
With hydrogen In methanol at 17 - 25℃; for 2.5h; Inert atmosphere; 3-Methoxy-l-methyl-4-nitropyrazole (2.9 g) was dissolved in MeOH (100 ml) at room temperature and Pd/C (0.58 g, 50% wet) was added. The solution was purged with nitrogen for 10 minutes, followed by hydrogen for 2.5 hours. The reaction mixture was filtered through a cake of celite, washed with EtOAc (200ml) and the volatiles removed under vacuum to give the crude product as a deep red oil. Column chromatography (SiO2; 50:50, EtOAc: heptane), followed by further purification via a 'catch and release' method (2g isolute flash SCX-2, eluting with 100% MeOH then methanolic ammonia (0.5M to 7M) furnished 3-methoxy-l-methylpyrazol-4-amine as a deep blue liquid (0.55Ig). NMR Spectrum: (CDCl3) 2.35 (m, 2H), 3.62 (s, 3H), 3.94 (s, 3H), 6.83 (s, IH); Mass spectrum: MH+ 128.
1.2 g With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 5h; 4 Step 4: Add a catalytic amount of palladium on carbon (55% humidity, 10% palladium) to a solution of 3-methoxy-1-methyl-4-nitro-1H-pyrazole (0.15g, 1mmol) in methanol (10mL) Content), after replacing the system with hydrogen for 3 times, the reaction was stirred at room temperature for 5 hours, filtered through Celite, and the filtrate was concentrated to obtain 1.2 g of light purple oily 3-methoxy-1-methyl-1H-pyrazole-4-amine. The yield is 95%,
  • 3
  • 5-methoxy-4-nitro-1H-pyrazole [ No CAS ]
  • [ 74-88-4 ]
  • [ 1201935-85-4 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In acetone at 60℃; for 10h; 3 Step 3: To 3-methoxy-4-nitro-1H-pyrazole (0.14g, 1mmol) in acetone (5mL) was added methyl iodide (0.3g, 2mmol) and potassium carbonate (0.3g, 2.2 mmol), the reaction was carried out at 60 degrees Celsius for 10 hours, cooled, filtered, and concentrated to obtain 0.15 g of light yellow oily 3-methoxy-1-methyl-4-nitro-1H-pyrazole, which was used directly in the next step .
  • 4
  • [ 1201935-85-4 ]
  • 2-(4-(2-hydroxyethyl)piperazin-1-yl)-N-(3-(2-((3-methoxy-1-methyl-1H-pyrazole-4-yl)amino)-5-methylpyrimidin-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl)butanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 100 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 4: trichlorophosphate / 3 h / 80 °C 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 0.5 h / 90 °C / Inert atmosphere 6: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 110 °C / Sealed tube; Inert atmosphere 7: ammonium formate; palladium 10% on activated carbon / methanol / 3 h / 75 °C / Inert atmosphere
  • 5
  • [ 1201935-85-4 ]
  • N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)-4-((4-methoxybenzyl)oxo)-5-methylpyrimidine-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 100 °C / Inert atmosphere
  • 6
  • [ 1201935-85-4 ]
  • 2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)-5-methylpyrimidine-4-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 100 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C
  • 7
  • [ 1201935-85-4 ]
  • 4-chloro-N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)-5-methylpyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 100 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 4: trichlorophosphate / 3 h / 80 °C
  • 8
  • [ 1201935-85-4 ]
  • 4-(7-chloro-1-tosyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)-5-methylpyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 100 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 4: trichlorophosphate / 3 h / 80 °C 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 0.5 h / 90 °C / Inert atmosphere
  • 9
  • [ 1201935-85-4 ]
  • 2-(4-(2-(benzyloxy)ethyl)piperazin-1-yl)-N-(3-(2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)-5-methylpyrimidin-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl)butanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 100 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 4: trichlorophosphate / 3 h / 80 °C 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 0.5 h / 90 °C / Inert atmosphere 6: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 110 °C / Sealed tube; Inert atmosphere
  • 10
  • [ 1201935-85-4 ]
  • 4-(7-chloro-1-tosyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: toluene-4-sulfonic acid / 1,4-dioxane / 100 °C
  • 11
  • [ 1201935-85-4 ]
  • (R)-N-(3-(2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-2-(4-methylpiperazin-1-yl)propionamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: toluene-4-sulfonic acid / 1,4-dioxane / 100 °C 3: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 100 °C
  • 12
  • [ 1201935-85-4 ]
  • 4-(7-chloro-1H-pyrrolo[2,3-c]pyridin-3-yl)-N-(3-methoxy-1-methyl-1H-pyrazole-4-yl)-5-methylpyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: hydrogenchloride / isopropyl alcohol
  • 13
  • [ 1201935-85-4 ]
  • 5-fluoro-N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)-4-((4-methoxybenzyl)oxo)pyrimidine-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 100 °C / Inert atmosphere
  • 14
  • [ 1201935-85-4 ]
  • 5-fluoro-2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)pyrimidine-4-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 100 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C
  • 15
  • [ 1201935-85-4 ]
  • 4-chloro-5-fluoro-N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 100 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 4: trichlorophosphate / 3 h / 80 °C
  • 16
  • [ 1201935-85-4 ]
  • 4-(7-chloro-1-tosyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-5-fluoro-N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 100 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 4: trichlorophosphate / 3 h / 80 °C 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 0.5 h / 90 °C / Inert atmosphere
  • 17
  • [ 1201935-85-4 ]
  • N-(3-(2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)-5-methylpyrimidin-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-2-(4-(oxobutan-3-yl)piperazin-1-yl)butanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C 2: hydrogenchloride / isopropyl alcohol 3: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 110 °C / Sealed tube; Inert atmosphere
  • 18
  • [ 1201935-85-4 ]
  • 5-amino-3-methoxy-1-methyl-4-nitropyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 3-methoxy-1-methyl-4-nitro-1H-pyrazole With 4-amino-1,2,4-triazole In dimethyl sulfoxide at 60℃; Stage #2: With potassium-t-butoxide In dimethyl sulfoxide at 60℃; for 4h; regioselective reaction; General procedure for the synthesis of compounds 2b-2j (taking 2b as an example) General procedure: 1-methyl-4-nitropyrazole (127 mg, 1 mmol) and 4-amino-1,2,4-triazole (303 mg, 3.6 mmol) were dissolved in DMSO (4 mL)to form a colorless solution, then heated the solution to 60 °C. Subsequently, potassium t-butoxide (449 mg, 4 mmol) wasslowly added to the reaction mixture in batches. The clear colorless solution promptly turned to a dark crimson red color asthe base dissolved. After 4 h of stirring at 60 °C, the reaction was quenched by ice water (150 mL) and acidified to pH=3with 10% HCl. Then the solution was extracted with ethyl acetate (50 mL, 3 times) and washed with saturated sodium chloride solution (30 mL, 2 times). Combined organic extracts were dried with anhydrous Na2SO4 and solvent evaporatedto give pure product 2b as red solid without further purification. 2c-2j were synthesized using a similar procedure.
88% With 4-amino-1,2,4-triazole; potassium-t-butoxide In dimethyl sulfoxide at 25℃; for 4h; 3 Synthesis of 5-amino-1-methyl-4-nitropyrazole (2a) General procedure: Acetonitrile (4mL) was added to 1-methyl-4-nitropyrazole (commercially available, 1a) (127 mg, 1 mmol) to dissolve it completely, and then added 4-amino-1,2,4-triazole (303 mg, 3.6 mmol) to the system, and dissolved it under stirring. Potassium tert-butanol (449 mg, 4 mmol) was then slowly added to it in batches. After adding, heat up to 60 °C and stir for 4h. After the reaction is complete, the reaction solution is poured into ice water (150mL) and then acidified with 10% dilute hydrochloric acid to pH = 3. The mixture was extracted with ethyl acetate (50mL, 3 times), followed by a saturated NaCl solution (30mL, 2 times) washed with the extract, anhydrous sodium sulfate dried, and the solvent was removed by rotary distillation to obtain a solid crude product. Finally, the crude product was separated and purified by column chromatography to obtain 5-amino-1-methyl-4-nitropyrazole (2a) (99.4mg, 70%), which was a red solid.
  • 19
  • [ 1201935-85-4 ]
  • (2R,3'R,4S)-4-fluoro-N-(3-(2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)pyrimidine-4- yl)-1H-indol-7-yl)[1,3'-bipyrrolidine]-2-carboxamide [ No CAS ]
  • (2R,3'S,4S)-4-fluoro-N-(3-(2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-1H-indol-7-yl)[1,3'-bipyrrolidine]-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: palladium 10% on activated carbon; hydrazine hydrate monohydrate / ethanol; ethyl acetate / 16 h / 20 °C 2.1: Palladium(0) bis(dibenzylideneacetone); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; Cs2CO3 / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 3.1: glacial acetic acid; zinc / ethanol / 1 h / 20 °C / Cooling with ice 4.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5.2: Resolution of racemate
  • 20
  • [ 1201935-85-4 ]
  • (2R,4S)-4-fluoro-N-(3-(2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)pyrimidine-4-yl)-1H-indol-7-yl)-1-(1-methylpiperidin-4-yl)pyrrolidine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: palladium 10% on activated carbon; hydrazine hydrate monohydrate / ethanol; ethyl acetate / 16 h / 20 °C 2: Palladium(0) bis(dibenzylideneacetone); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; Cs2CO3 / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 3: glacial acetic acid; zinc / ethanol / 1 h / 20 °C / Cooling with ice 4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
  • 21
  • [ 1201935-85-4 ]
  • 3-methoxy-1-methyl-1H-pyrazol-4-amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With palladium 10% on activated carbon; hydrazine hydrate monohydrate In ethanol; ethyl acetate at 20℃; for 16h; 1.5 Synthesis of 3-methoxy-1-methyl-4-amino-1H-pyrazole To a solution of 3-methoxy-1-methyl-4-nitro-1H-pyrazole (3.8 g, 24.2 mmol) in EtOAc/EtOH (40 mL/10 mL),Palladium on carbon (10% Pd/C, 55% water, 1.0 g) and hydrazine hydrate (8 mL) were added, and the mixture was reacted at room temperature for 16 h.After the reaction was completed, it was filtered and the filter residue was washed with EtOAc.The combined filtrates were concentrated under reduced pressure, the resulting residue was dissolved in EtOAc, and HCl/EtOAc was added dropwise with rapid stirring until the precipitation was complete. After filtration, the filter residue was washed with EtOAc and acetonitrile (MeCN) to obtain 3.5 g of the hydrochloride salt of the product. Yield 89%.
  • 22
  • [ 1201935-85-4 ]
  • 3-{2-[(3-methoxy-1-methyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl}-1H-indol-7-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrazine hydrate monohydrate / ethanol; ethyl acetate / 16 h / 20 °C 2: Palladium(0) bis(dibenzylideneacetone); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; Cs2CO3 / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 3: glacial acetic acid; zinc / ethanol / 1 h / 20 °C / Cooling with ice
  • 23
  • [ 1201935-85-4 ]
  • 3-(2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)-5-methylpyrimidin-4-yl)-1H-indol-7-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: palladium 10% on activated carbon; hydrazine hydrate monohydrate / ethanol; ethyl acetate / 16 h / 20 °C 2.1: Palladium(0) bis(dibenzylideneacetone); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; Cs2CO3 / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Cooling with ice 3.2: 6 h / 20 °C / Cooling with ice 4.1: glacial acetic acid; zinc / ethanol / 1 h / 20 °C / Cooling with ice
  • 24
  • [ 1201935-85-4 ]
  • (2R,4S)-4-fluoro-N-(3-(2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)-5-methylpyrimidine-4 -yl)-1H-indol-7-yl)pyrrolidine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: palladium 10% on activated carbon; hydrazine hydrate monohydrate / ethanol; ethyl acetate / 16 h / 20 °C 2.1: Palladium(0) bis(dibenzylideneacetone); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; Cs2CO3 / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Cooling with ice 3.2: 6 h / 20 °C / Cooling with ice 4.1: glacial acetic acid; zinc / ethanol / 1 h / 20 °C / Cooling with ice 5.1: pyridine; 1-propanephosphonic acid cyclic anhydride / ethyl acetate / 18 h / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 25
  • [ 1201935-85-4 ]
  • N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)-4-(7-nitro-1H-indol-3-yl)pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrazine hydrate monohydrate / ethanol; ethyl acetate / 16 h / 20 °C 2: Palladium(0) bis(dibenzylideneacetone); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; Cs2CO3 / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere
  • 26
  • [ 1201935-85-4 ]
  • N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)-5-methyl-4-(7-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-3-yl)pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrazine hydrate monohydrate / ethanol; ethyl acetate / 16 h / 20 °C 2: Palladium(0) bis(dibenzylideneacetone); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; Cs2CO3 / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere
  • 27
  • [ 1201935-85-4 ]
  • N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)-5-methyl-4-(7-nitro-1H-indol-3-yl)pyrimidine-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: palladium 10% on activated carbon; hydrazine hydrate monohydrate / ethanol; ethyl acetate / 16 h / 20 °C 2.1: Palladium(0) bis(dibenzylideneacetone); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; Cs2CO3 / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Cooling with ice 3.2: 6 h / 20 °C / Cooling with ice
  • 28
  • [ 1201935-85-4 ]
  • tert-butyl (2R,4S)-4-fluoro-2-((3-(2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)-5-methylpyrimidin-4-yl)-1H-indol-7-yl)carbamoyl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: palladium 10% on activated carbon; hydrazine hydrate monohydrate / ethanol; ethyl acetate / 16 h / 20 °C 2.1: Palladium(0) bis(dibenzylideneacetone); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; Cs2CO3 / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Cooling with ice 3.2: 6 h / 20 °C / Cooling with ice 4.1: glacial acetic acid; zinc / ethanol / 1 h / 20 °C / Cooling with ice 5.1: pyridine; 1-propanephosphonic acid cyclic anhydride / ethyl acetate / 18 h / 20 °C
  • 29
  • [ 1201935-85-4 ]
  • tert-butyl (2R,4S)-4-fluoro-2-((3-(2-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)pyrimidine-4-yl)-1H-indol-7-yl)carbamoyl)[1,3'-bipyrrolidine]-1'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: palladium 10% on activated carbon; hydrazine hydrate monohydrate / ethanol; ethyl acetate / 16 h / 20 °C 2: Palladium(0) bis(dibenzylideneacetone); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; Cs2CO3 / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 3: glacial acetic acid; zinc / ethanol / 1 h / 20 °C / Cooling with ice 4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
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