Category: 181585-93-3

Application of 181585-93-3,Some common heterocyclic compound, 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, molecular formula is C5H5N3O4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step3: Methyl 5,7-dihydroxy-6-phenylpyrazolo[1 ,5-a]pyrimidine-2-carboxylate; A solution of 5.Og Methyl 3-amino-1 H-pyrazole-5-carboxylate, 8.3ml_ diethyl- phenylmalonate and 5OmL diisopropylethylamine in 5OmL DMF was heated to 1500C for 40h. The solvent was removed, the solid residue was dissolved in 2- propanol the mixture was stirred for 3 hours. The desired product was filtered, dried and was used without further purification. MS (M+1): 286 Characteristic 1 H NMR (300MHz, d6-DMSO) signals: 6.0 (s, 1 H); 3.8 (s, 3H)

The synthetic route of 181585-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; VENNEMANN, Matthias; MAIER, Thomas; HOeLDER, Swen; BENEKE, Gerrit; DEHMEL, Florian; ZUeLCH, Armin; STRUB, Andreas; BECKERS, Thomas; INCE, Stuart; REHWINKEL, Hartmut; LIU, Ningshu; BOeMER, Ulf; WO2010/91808; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 181585-93-3, The chemical industry reduces the impact on the environment during synthesis 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

5-Nitro-3-pyrazole-carboxylic acid methyl ester (22.35 g, 130.61 mmol) is dissolved in each 160 mL THF und glacial acetic acid. Then, Pd-C (10%, 4.36 g) are added and the reaction is stirred for 6 days under hydrogen atmosphere at RT. Then, the mixture is filtered over celite and the solvent is removed under vacuum. The crude material is dissolved in methylene chloride (800 mL) and sodium hydrogen carbonate (200 g) are added, filtered and the solvent is again removed under vacuum. This procedure is repeated until the acetic acid smell is lost. 5-Amino-3-pyrazole-carboxylic acid methyl ester is isolated in high yields (16.91 g, 91.7%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 5-nitro-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; US2008/32998; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 181585-93-3, SDS of cas: 181585-93-3

Methyl 3-nitro-1H-pyrazole-5-carboxylate (1.71 g,10 mM) was dissolved in methanol (40 mL), and 10% Pd/C (0.26 g) was added. Hydrogenation wascarried out in a Paar apparatus under 5 bar. After 24 h, the catalyst was filtered o and washedby methanol. The solvent was evaporated by reduced pressure, and the residue was crystallizedfrom ethanol (10 mL). Yield: 1.14 g, 81%. Melting point by DSC: 116 and 142 C (Figure S23). TLC:CHCl3/MeOH/AcOH (90:8:2) Rf = 0.43. Elemental analysis for C5H7N3O2: calculated C, 42.55%; H,4.96%; N, 29.79%; found: C, 42.70%; H, 5.00%; N, 29.71%. 1H NMR (400MHz, DMSO-d6) delta(ppm):tautomer T5; 12.16 (1H, s, N-HPz), 5.68 (1H, s, C-HPz), 5.19 (2H, s, NH2), 3.75 (3H, s, CH3), tautomerT3; 12.60 (1H, s, N-HPz), 5.92 (1H, s, C-HPz), 4.81 (2H, s, NH2), 3.75 (3H, s, CH3) (Figure S15). 13CNMR (400 MHz, DMSO-d6)delta (ppm): tautomer T5; 159.65 (C=O), 148.85 (C-NH2), 132.54 (C-C=O),89.04 (C4-H), tautomer T3; 162.87 (C=O), 156.20 (C-NH2), 142.35 (C-C=O), 94.27 (C4-H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Kusakiewicz-Dawid, Anna; Porada, Monika; Dziuk, B?azej; Siod?ak, Dawid; Molecules; vol. 24; 14; (2019);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 181585-93-3

To a solution of 2-methyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester and 1-methyl-5-nitro-1H-pyrazole-3-carboxylic acid methyl ester (1.18 g, 6.37 mmo 1) in tetrahydro furan (20 mL) at 0C was added a lithium aluminum hydride solution (1 .OM in tetrahydrofuran, 7.65 mL, 7.65 mmol) drop wise. The resulting mixture was stirred at 0C for 20 min. To this solution was added ethyl acetate (1 mL) followed by few crystals of sodium sulphate decahydrate. The resulting mixture was stirred for 30 min then filtered, the filter cake washed with ethyl acetate and the filtrate evaporated. The residue was purified by flash chromatography (silica gel, 80 g, 50% to 70% ethyl acetate in hexanes) to give 1-methyl-3-nitro-1H-pyrazol-5-yl)methanol (496 mg, 50%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 3.90 (s, 3 H) 4.53 (d, J=5.67 Hz, 2 H) 5.55 (t, J=5.48 Hz, 1 H) 6.93 (s, 1 H).

The synthetic route of 181585-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BROTHERTON-PLEISS, Christine; JAIME-FIGUEROA, Saul; LOPEZ-TAPIA, Francisco Javier; LOU, Yan; OWENS, Timothy D.; WO2013/24078; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 181585-93-3

To a solution of 2-methyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester and 1-methyl-5-nitro-1H-pyrazole-3-carboxylic acid methyl ester (1.18 g, 6.37 mmo 1) in tetrahydro furan (20 mL) at 0C was added a lithium aluminum hydride solution (1 .OM in tetrahydrofuran, 7.65 mL, 7.65 mmol) drop wise. The resulting mixture was stirred at 0C for 20 min. To this solution was added ethyl acetate (1 mL) followed by few crystals of sodium sulphate decahydrate. The resulting mixture was stirred for 30 min then filtered, the filter cake washed with ethyl acetate and the filtrate evaporated. The residue was purified by flash chromatography (silica gel, 80 g, 50% to 70% ethyl acetate in hexanes) to give 1-methyl-3-nitro-1H-pyrazol-5-yl)methanol (496 mg, 50%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 3.90 (s, 3 H) 4.53 (d, J=5.67 Hz, 2 H) 5.55 (t, J=5.48 Hz, 1 H) 6.93 (s, 1 H).

The synthetic route of 181585-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BROTHERTON-PLEISS, Christine; JAIME-FIGUEROA, Saul; LOPEZ-TAPIA, Francisco Javier; LOU, Yan; OWENS, Timothy D.; WO2013/24078; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 5-nitro-1H-pyrazole-3-carboxylate

2-tert-Butoxycarbonylmethyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester: To a stirring mixture of delta-nitro^H-pyrazole-S-carboxylic acid methyl ester ( 3.5 gm, 20.5 mmol) dissolved in 150 ml of acetone was added cesium carbonate ( 8.01 gm, 24.6 mmol) followed by the addition of tert-butyl bromoacetate ( 3.61 ml). After 5 hours the solids were filtered and the mixture chromatographed on silica gel using 10% ethyl acetate/hexanes as the eluent to obtain 4.16 gm of pure title product. ESI M+1= 286.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SCHERING CORPORATION; WO2006/50034; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 181585-93-3, The chemical industry reduces the impact on the environment during synthesis 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

[00125] delta-Nitro-S-pyrazole-carboxylic acid methyl ester (22.35 g, 130.61 mmol) is dissolved in 160 ml_ THF und 160 ml_ glacial acetic acid. Then, Pd-C (10%, 4.36 g) is added and the reaction is stirred for 6 days under hydrogen atmosphere at RT. Then, the mixture is filtered over celite and the solvent is removed under vacuum. The crude material is dissolved in methylene chloride (800 ml_) and sodium hydrogen carbonate (200 g) is added, filtered and the solvent is again removed under vacuum. This procedure is repeated until the acetic acid smell is lost. delta-Amino-S-pyrazole-carboxylic acid methyl ester is isolated in high yields (16.91 g, 91.7 %)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 5-nitro-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; WEIL, Tanja; HECHENBERGER, Mirko; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; ERDMANE, Elina; SMITS, Gints; WO2011/15343; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 181585-93-3,Some common heterocyclic compound, 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, molecular formula is C5H5N3O4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

a) 5-Nitro-2-(3,4,5-trifluoro-benzyl)-2H-pyrazole-3-carboxylic acid methyl ester A mixture of methyl-3-nitro-1-H-pyrazole-5-carboxylate (ART-CHEM) (600 mg, 3.5 mmol), 3,4,5-trifluoromethylbenzyl bromide (789 mg, 3.5 mmol) and cesium carbonate (1.37 g, 4.2 mmol) in 15 ml of acetonitrile was stirred at 60 C. for 2 hours. The reaction mixture was concentrated, hydrolyzed and extracted with ethyl acetate. The organic phase was dried, evaporated and the residue triturated with diethyl ether to yield the title compound as a colorless solid (698 mg, Yield=63%). MS ISP (m/e): 333.1 (100) [(M+NH4)+]. 1H NMR (CDCl3, 300 MHz): delta (ppm)=7.43 (s, 1H), 7.04 (t, 2H), 5.75 (s, 2H), 3.95 (s, 3H).

The synthetic route of 181585-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baumann, Karlheinz; Goetschi, Erwin; Jolidon, Synese; Limberg, Anja; Luebbers, Thomas; US2010/120874; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 181585-93-3,Some common heterocyclic compound, 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, molecular formula is C5H5N3O4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of methyl 3-nitro- 1H-pyrazole-5-carboxylate (500 mg) in Ethanol (0.25M) was added 10% Palladium on Carbon (0.1 eq) and ammonium fomiate (8 eq) and the reaction was heated for 1 hour at 70C then cooled to room temperature, filtered through celite, rinsed withMethanol and concentrated to dryness. The crude intermediate was suspended in DCM and extracted with water. To the organic layer was added 3 eq of MP-TsOH catch and release resin whereupon the mixture was stirred for 1 hour, filtered to collect resin then eluted with 7N Ammonia in MeOH and concentrated to dryness to afford 100 mg of methyl 3-amino-1H-pyrazole-5-carboxylate. To a solution of methyl3-amino-1H-pyrazole-5-carboxylate in dioxane was added di-tert-butyl dicarbonate (1.5 eq) and the reaction was heated at 120C overnight, then stirred at room temperature for 6 hours before the addition of imidazole (4.5 eq). The reaction mixture was subsequently refluxed at 130C for 2 hrs then stirred at room temperature overnight, concentrated to dryness, suspended in Ethyl acetate and extracted 3x with 0.25N HC1 solution, dried, filtered and concentrated to afford 427 mg ofmethyl 3-Qert-butoxycarbonylamino)-1H-pyrazole-5-carboxylate as a light pink solid. Similar to as described in General Procedure A, 3-(tert-butoxycarbonylamino)- 1H-pyrazole-5-carboxylate (200 mg) was reacted with 2-fluoro-4-iodo-pyridine to give methyl 5-(tert-butoxycarbonylamino)- 1 -(4-iodo-2-pyridyl)pyrazole-3-carboxylate. The crude material was used directly in subsequent reactions. To a solution of5-(tertbutoxycarbonylamino)-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylate in DCM was added 4NHC1 in dioxane (10 eq). The reaction was stirred at room temperature for 30 minutes thenconcentrated to dryness to afford crude methyl5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylate as the HC1 salt. Similar to as described inGeneral Procedure J, methyl 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylate was reacted toafford 90 mg 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylic acid which was used in the nextstep without purification. Similar as to described in General Procedure B, 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylic acid was reacted with ammonium chloride to afford 90 mg of 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxamide which was used in the next reaction without purification.Similar to as described in General Procedure E, 5-amino-1-(4-iodo-2-pyridyl) pyrazole-3-carboxamide (90 mg) was reacted with (3R)-3-ethynyl-3-hydroxy-1-methyl-pyrrolidin-2-one to give 14mg of the title compound (15%). M-i-H = 341.0; 1H NMR (400 MHz, DMSO-d6) oe 8.44 (dd, J= 5.2, 0.8 Hz, 1H), 8.03- 8.00 (m,1H), 7.68 (s, 1H), 7.29, (dd, J= 5.1, 1.5 Hz, 1H), 7.21 (s, 1H), 6.89 (s, 2H), 6.63 (s, 1H), 5.72 (s,1H), 3.41 – 3.34 (m, 2H), 2.81 (s, 3H), 2.48 – 2.43 (m, 1H), 2.26 – 2.17 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-nitro-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 5-nitro-1H-pyrazole-3-carboxylate

To a solution ofmethyl3-nitro-1H-pyrazole-5-carboxylate (342 mg, 2.0 mmol) macetone (40 mL) was added 1,2-dibromoethane (412 mg, 2.2 mmol), followed by K2C03 (828mg, 6. 0 mmol). The resulting mixture was stirred to reflux for 2 hrs. Then K2C03 was filteredoff The filtrate was concentrated in vacuo to give a residue, which was purified by silica gelcolumn (DC.lV1/MeOH = 50/1) to afford methyll-(2-bromoethyl)-3-nitro-lH-pyrazole-5-carboxylate (430 mg, yield: 77%) as yellow solid.[001034] 1H NMR (400 rviHz, CDCb): J = 7.42 (s, 1H), 5.08 (t, J = 6.4 Hz, 2H), 3.97 (s, 3H),3.78 (t, J = 6.4 Hz, 2H).

The synthetic route of 181585-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JECURE THERAPEUTICS, INC.; STAFFORD, Jeffrey A.; VEAL, James M.; TRZOSS, Lynnie Lin; MCBRIDE, Christopher; (411 pag.)WO2018/136890; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics