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Chemical Structure| 129488-09-1

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Product Details of [ 129488-09-1 ]

CAS No. :129488-09-1
Formula : C12H13N3O4
M.W : 263.25
SMILES Code : O=C(N1N=CC2=C1C=CC([N+]([O-])=O)=C2)OC(C)(C)C
MDL No. :MFCD07779196
InChI Key :YXAJFAVMXBRTMU-UHFFFAOYSA-N
Pubchem ID :11499917

Safety of [ 129488-09-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 129488-09-1 ]

* 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 [ 129488-09-1 ]

[ 129488-09-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 129488-09-1 ]
  • [ 129488-10-4 ]
YieldReaction ConditionsOperation in experiment
100% In methanol; palladium; ethyl acetate; Part B Preparation of 5-amino-indazole-1-carboxylic acid t-butyl ester In a Paar flask charged with palladium (10 wt percent on carbon, 0.44 g) was added ethyl acetate (30 mL) and 5-nitro-indazole-1-carboxylic acid t-butyl ester (1.61 g, 6.2 mmol). The reaction mixture was hydrogenated at 50 psi for 30 minutes with vigorous shaking. The reaction mixture was filtered through a plug of celite. The plug was washed with 20 mL of methanol and the combined filtrates were concentrated in vacuo to give a white solid (1.4 g, 100percent). 1H NMR (300 MHz, CDCl3), delta: 7.99 (s, 1H), 7.97 (d, J=10, 1H), 6.94 (dd, J=10, J'=2, 1H), 6.92 (d, J=2, 1H), 1.71 (s, 9H).
98.6% With palladium 10% on activated carbon; hydrogen; In methanol; Compound Reg-1-1-b (38 g, 144.35 mmol) was dissolved in methanol (700 mL), Pd/C (3.8 g, 10percent water) wasadded, purge with hydrogen was performed for three times, and the reaction was performed under a hydrogen atmosphereovernight. Thin layer chromatography (petroleum ether : ethyl acetate=3:1) indicated the reaction was complete. Thereaction solution was filtered through Celite to afford compound Reg-1-1-c (33.2 g, brown solid, yield: 98.6percent).1H NMR (400 MHz, CDCl3) delta 7.97 (d, J = 10.8 Hz, 2H), 7.00 - 6.87 (m, 2H), 3.74 (s, 2H), 1.71 (s, 9H).
98.6% With palladium on activated charcoal; hydrogen; In methanol; water; Compound Reg-1-1-b (38 g, 144.35 mmol) was dissolved in methanol (700 mL), Pd/C (3.8 g, 10percent water) was added, purge with hydrogen was performed for three times, and the reaction was performed under a hydrogen atmosphere overnight. Thin layer chromatography (petroleum ether : ethyl acetate=3:1) indicated the reaction was complete. The reaction solution was filtered through Celite to afford compound Reg-1-1-c (33.2 g, brown solid, yield: 98.6percent). 1H NMR (400 MHz, CDCl3) delta 7.97 (d, J = 10.8 Hz, 2H), 7.00 - 6.87 (m, 2H), 3.74 (s, 2H), 1.71 (s, 9H).
With hydrogen;palladium on activated charcoal; In tetrahydrofuran; at 40℃; under 2585.81 Torr; for 16h; To a solution of 5-nitro-indazole-1 -carboxylic acid tert-butyl ester (300 g, 1 .1 mol, 1 .0 eq) in THF (3 L), and the mixture was hydrogenated at 40 °C with Pd/C (30 g) as catalyst in the presence of H2 (50 psi). The reaction mixture was stirred at 40 °C fori 6 hrs. TLC (PE: EA=4:1 ) showed the reaction was complete. After uptake of H2, the catalyst was filtered off and the filtrate was evaporated to afford the crude 5-amino-indazole-1 -carboxylic acid tert-butyl ester (252 g, 95percent) which was used directly for next step without purification.
With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 40℃; under 2585.81 Torr; for 16h; To a solution of 5-nitro-indazole-1-carboxylic acid tert-butyl ester (300 g, 1.1 mol, 1.0 eq) in THF (3 L), and the mixture was hydrogenated at 40° C. with Pd/C (30 g) as catalyst in the presence of H2 (50 psi). The reaction mixture was stirred at 40° C. for 16 hrs. TLC (PE:EA=4:1) showed the reaction was complete. After uptake of H2, the catalyst was filtered off and the filtrate was evaporated to afford the crude 5-amino-indazole-1-carboxylic acid tert-butyl ester (252 g, 95percent) which was used directly for next step without purification.
With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 40℃; under 2585.81 Torr; for 16h; To a solution of 5-nitro-indazole-1-carboxylic acid tert-butyl ester (300 g, 1.1 mol, 1.0 eq) in THF (3 L) was added Pd/C (30 g). The reaction mixture was stirred at 40°C for 16 hours under pressure of H2 (50 psi). TLC (PE: EtOAc = 4:1) showed complete conversion. After uptake of H2, the catalyst was filtered off and the filtrate was evaporated to afford the crude 5-amino-indazole-1-carboxylic acid tert-butyl ester (252 g, 95percent) which was used directly for next step without purification.
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20℃; for 3h; [0003711 To a stirred solution of compound 2 (1 g, 1 eq) in ethyl acetate (30 mL), 10percentPd-C (0.28 g) was added under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 3 h under hydrogen atmosphere (balloon pressure). The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and evaporated under reduced pressure to afford the title compound 3.

 

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