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Product Details of [ 58793-45-6 ]

CAS No. :58793-45-6
Formula : C5H7N3O2
M.W : 141.13
SMILES Code : O=[N+](C1=CN(CC)N=C1)[O-]
MDL No. :MFCD08559107

Safety of [ 58793-45-6 ]

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

Application In Synthesis of [ 58793-45-6 ]

* 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 [ 58793-45-6 ]

[ 58793-45-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 58793-45-6 ]
  • [ 876343-24-7 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen;palladium 10% on activated carbon; In ethanol; under 2585.81 Torr; for 3h;Inert atmosphere; Example 111b l-Ethyl-lH-pyrazol-4-amine 111b CGI PHARM6 0WOA 250-mL Parr reactor bottle was purged with nitrogen and charged with 10% palladium on carbon (50% wet, 468 mg dry weight) and a solution of 111a (1.90 g, 13.5 mmol) in ethanol (100 mL). The bottle was attached to a Parr hydrogenator, evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 3 h. After this time, the hydrogen was evacuated, and nitrogen was charged into the bottle. Celite 521 (1.00 g) was added, and the mixture was filtered through a pad of Celite 521. The filter cake was washed with ethanol (2 x 25 mL), and the combined filtrates were concentrated to dryness under reduced pressure to afford a quantitative yield of 111b (1.50 g) as a purple oil: ]H NMR (300 MHz, CDC13) delta 7.15 (s, 1H), 7.02 (s, 1H), 4.05 (q, 2H, / = 7.2 Hz), 2.88 (br s, 2H), 1.43 (t, 3H, / = 7.2 Hz); MS (ESI+) m/z 112.1 (M+H).
96% With palladium 10% on activated carbon; hydrogen; In methanol; at 25℃; for 12h; Under hydrogen (1 atm), to a solution of compound 40-b (1.0 g, 7.1 mmol) in methanol (10 mL) was added 10% Pd-C (0.1 g). The mixture was stirred at 25 C. for 12 hours, and then filtrated, the filtrate was concentrated under reduced pressure to give compound 40-a (760 mg, yield: 96%), which was used directly for the next step without purification. LC-MS (ESI): m/z=112 [M+H]+.
93% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 6h; Example 123b 1-Ethyl-1H-pyrazol-4-amine 123b A 100-mL single-neck round-bottomed flask was purged with hydrogen and charged with 123a (4.5 g, 31.9 mmol), 10% palladium on carbon (10% wet, 2.0 g), and methanol (50 mL). The mixture was stirred at room temperature for 6 h. The catalyst was removed by filtration through a pad of CELITE and the filtrate was concentrated under reduced pressure to afford 123b (3.3 g, 93%). MS-ESI: [M+H]+ 112.0
89% With hydrogen;platinum(IV) oxide; In ethanol; ethyl acetate; under 2280.15 Torr; for 2h; A mixture of a portion (0.8 g) of the material so obtained, platinum oxide (0.1 g), ethyl acetate (10 ml) and ethanol (30 ml) was stirred under 3 atmospheres pressure of hydrogen for5 2 hours. The catalyst was removed by filtration and the filtrate was evaporated. There was thus obtained the required starting material in 89% yield; 1H NMR: (DMSOd6) 1.27 (t, 3H), 3.77 (br s, 2H), 3.92 (q, 2H), 6.87 (s, IH), 7.01 (s, IH).
89% With hydrogen;platinum(IV) oxide; In ethanol; ethyl acetate; under 2280.15 Torr; for 2h; A mixture of a portion (0.8 g) of the material so obtained, platinum oxide (0.1 g), ethyl acetate (10 ml) and ethanol (30 ml) was stirred under 3 atmospheres pressure of hydrogen for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated. There was thus obtained the required starting material in 89% yield; 1HNMR: (DMSOd6) 1.27 (t, 3H), 3.77 (br s, 2H), 3.92 (q, 2H), 6.87 (s, IH), 7.01 (s, IH).
89% With hydrogen;platinum(IV) oxide; In ethanol; ethyl acetate; under 2280.15 Torr; for 2h; A mixture of a portion (0.8 g) of the material so obtained, platinum oxide (0.1 g), ethyl acetate (10 ml) and ethanol (30 ml) was stirred under 3 atmospheres pressure of hydrogen for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated. There was thus obtained the required starting material in 89% yield; 1H NMR: (DMSOd6) 1.27 (t, 3H), 3.77 (br s, 2H), 3.92 (q, 2H), 6.87 (s, 1H), 7.01 (s, 1H).
89% With hydrogen;platinum(IV) oxide; In ethanol; ethyl acetate; under 2280.15 Torr; for 2h; A mixture of a portion (0.8 g) of the material so obtained, platinum oxide (0.1 g), ethyl acetate (10 ml) and ethanol (30 ml) was stirred under 3 atmospheres pressure of hydrogen for2 hours. The catalyst was removed by filtration and the filtrate was evaporated. There was thus obtained the required starting material in 89% yield; 1H NMR Spectrum: (DMSOd6) 1.27 (t, 3H), 3.77 (br s, 2H), 3.92 (q, 2H), 6.87 (s, IH), 7.01 (s, IH).
89% With hydrogen;platinum(IV) oxide; In ethanol; ethyl acetate; under 2280.15 Torr; for 2h; A mixture of a portion (0.8 g) of the material so obtained, platinum oxide (0.1 g), ethyl acetate (10 ml) and ethanol (30 ml) was stirred under 3 atmospheres pressure of hydrogen for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated. There was thus obtained the required starting material in 89% yield; 1H NMR Spectrum: (DMSOd6) 1.27 (t, 3H), 3.77 (br s, 2H), 3.92 (q, 2H), 6.87 (s, IH), 7.01 (s, IH).
87% With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 2h; Synthesis of Compound 5.2. Into a 250-mL round-bottom flask purged and maintained under an inert atmosphere of nitrogen, was placed 5.1 (1.9 g, 13.46 mmol, 1.00 equiv), methanol (100 mL), and palladium on carbon (200 mg). The flask was evacuated and flushed three times with nitrogen, followed by flushing with hydrogen. The reaction was stirred 2 h at room temperature under an atmosphere of hydrogen (balloon). Then the solids were filtered off and the organics were concentrated in vacuo. This afforded 1.3 g (87%) of 5.2 as red oil.
With hydrogen;palladium 10% on activated carbon; In ethanol; ethyl acetate; 4-Amino-l-ethyl-lfl-pyrazole"; [529] To a solution of l-ethyl-4-nitro-lF-pyrazole (59mg, 0.42mmol) in ethylacetate (2mL) and ethanol (2mL) was added W% Pd-C (20mg), and the resulting mixture wasstirred under hydrogen atmosphere overnight. TLC showed the reaction was complete. Thecatalyst was removed by filtration through a pad of celite, and the filtrate was concentratedunder reduced pressure to give the title compound as red oil. *H NMR (CDC13, 400 MHz): 8= 1.43 (t, J= 7.3 Hz, 3H), 2.90 (br s, 2H), 4.05 (q, J= 7.3 Hz, 2H), 7.02 (d, J= 0.8 Hz, 1H),7.15(d,J=0.8Hz, 1H).
260 mg With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 16h; To a solution of 4-nitro-lH-pyrazole (500 mg, 4.42 mmol) in anhydrous THF (20 mL) was added NaH (60% dispersion in mineral oil, 353 mg, 8.84 mmol) in portions at 0C . The resulting mixture was stirred at 0C for 10 min. Then 1-bromoethane (723 mg, 6.64mmol) in anhydrous THF (2 mL) was added dropwise at 0C . The mixture was stirred at ambient temperature for 16 h. Then reaction was quenched with H20 (20 mL) and the volatiles were removed under reduced pressure. The resulting aqueous layer was extracted with EA (2*30 mL). The combined extracts were concentrated under reduced pressure. The residue was dissolved in MeOH (30 mL) and then Pd/C (10%, 100 mg) was added. The mixture was stirred at ambient temperature under hydrogen atmosphere for 16 h. The catalyst was filtered off. The filtrate was concentrated and the residue was purified via ISCO (eluted with MeOH in H20 0-100%) to afford the title compound as brown oil (260 mg, 52.9% yield, 2 steps). MS (m/z): 112.1 (M+H)+.
260 mg With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 16h; To a solution of 4-nitro-lH-pyrazole (500 mg, 4.42 mmol) in anhydrous THF (20 mL) was added NaH (60% dispersion in mineral oil, 353 mg, 8.84 mmol) in portions at 0 C. The resulting mixture was stirred at 0 C for 10 min. Then 1-bromoethane (723 mg, 6.64 mmol) in anhydrous THF (2 mL) was added dropwise at 0 C. The mixture was stirred at ambient temperature for 16 h. Then reaction was quenched with H20 (20 mL) and the volatiles were removed under reduced pressure. The resulting aqueous layer was extracted with EA (2*30 mL). The combined extracts were concentrated under reduced pressure. The residue was dissolved in MeOH (30 mL) and then Pd/C (10%, 100 mg) was added. The mixture was stirred at ambient temperature under hydrogen atmosphere for 16 h. The catalyst was filtered off. The filtrate was concentrated and the residue was purified via ISCO (eluted with MeOH in H20 0-100%) to afford the title compound as brown oil (260 mg, 52.9% yield, 2 steps). MS (m/z): 112.1 (M+H)+.
With hydrazine hydrate; palladium 10% on activated carbon; In ethanol; at 80℃; for 0.166667h; General procedure: 80% hydrazine hydrate (1 mL) and 10% palladium charcoal (0.04 g) were added to a solution of 2a (2 mmol) in ethanol (5 mL). The reaction was hated to 80C for 10 min and filltered by celite. The filtrate was dried by sodium sulfate, and concentrated in vacuum to afford compound 3a, which were used without further purification.
With palladium 10% on activated carbon; hydrogen; In methanol; at 25℃; under 760.051 Torr; for 12h; Palladium 10% on carbon (0.1 g) was added to a solution of compound 13-c (1.0 g, 7.1 mmol) in methanol (10 mL) under hydrogen gas atmosphere (1 atm). The mixture was reacted at 25 C. for 12 hours, then filtered and the filtrate was concentrated under reduced pressure to give compound 13-b (760 mg, yield 96%), which was directly used for the next step without purification. LC-MS (ESI): m/z=112[M+H]+.

  • 2
  • [ 28466-26-4 ]
  • [ 58793-45-6 ]
  • [ 1338718-34-5 ]
YieldReaction ConditionsOperation in experiment
Example 41 5-Chloro-1-ethyl-4-nitro-1H-pyrazole Following the procedure for Intermediate 5 starting with 1-ethyl-4-nitropyrazole gave 5-chloro-1-ethyl-4-nitro-1H-pyrazole as a colorless solid (1.3 g, 74%). 1H-NMR (400 MHz, CDCl3) delta 8.16 (s, 1H), 4.26 (q, J=7 Hz, 2H), 1.50 (t, J=7 Hz, 3H).
 

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