Category: 37622-90-5

37622-90-5, name is Ethyl 4-pyrazolecarboxylate, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of Ethyl 4-pyrazolecarboxylate

[1326] to a solution of ethyl 1H-pyrazole-4-carboxylate (5 g, 35.68 mmol) and Cs2CO3 (23.25 g, 71.36 mmol) in DMF(100 ml) was added mel (10.13 g, 71.36 mmol, 4.44 ml). The mixture was stirred at 25c for 16h. The mixture was filtered, the filtrate was diluted with H2O (500 ml), extracted with ea (50 ml x 3), dried over Na2SO4, filtered and concentrated to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 5/1). Compound 282a (4.5 g, yield: 81.81%) was obtained as a yellow oil. 1H NMR (400mhz, CDCl3) delta 7.84 (d, = 8.5 hz, 2h), 4.24 (q, = 7.3 hz, 2h), 4.03-3.70 (m, 3h), 1.30 (t, j = 7.2 hz, 3h). MS (ESI) m/z (M+H)+155.0.

The synthetic route of 37622-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 37622-90-5, A common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, molecular formula is C6H8N2O2, its 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.

4-Ethylpyrazole carboxylate (10g, 71.40 mmol) is placed in an oven -dried flask under an atmosphere of argon. Dry THF (100 mL) is added followed by the dropwise addition of lithium aluminium hydride (1 M in THF, 100 mL, 100 mmol). Once the addition is complete the reaction mixture is stirred at 50C. The reaction is shown to be complete by NMR after 4 hours. The reaction mixture is cooled on an ice-bath and the reaction mixture is quenched with water (3.8 mL) then 15% sodium hydroxide (3.8 mL) and finally water again (11.4 mL). The solvent is removed in vacuo and the solid is placed in a Soxhlet apparatus. THF is refluxed through the system for 24 hours. The solvent is removed in vacuo to give the title compound.1H NMR (MeOD, 400 MHz); 7.60 (s, 2H), 4.55 (s, 2H).

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; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2008/6563; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 37622-90-5, A common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, molecular formula is C6H8N2O2, its 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.

Preparation 8; Preparation of HI-ftert-butoxycarbonylt°iperidin-^yll-IH-pyrazole-Phicarboxylic acid; A mixture of ethyl 1H-pyrazole-4-carboxylate (700 mg, 5 mmol) and NaH 60% (6 mmol) was stirred under nitrogen at 00C for 1 hour in dry DMF (15 mL). ferf-Butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (1.53 gr, 5.5 mmol) dissolved in 4 mL of dry DMF was added and the resulting solution was hetaed at 100C overnight . Reaction mixture was quenched with water and extracted (x3) with ethyl acetate. Collected organic phases were dried over Na2SU4, filtered and evaporated to dryness. Residue was dissolved in MeOH (20 mL) and water (5 mL) and KOH (1.12 gr, 20 mmol) was added. The resulting solution was stirred at room temperature 24 hours, then solvents removed under reduced pressure. The residue was taken-up with AcOEt and KHSO4 5% solution. Acqueous phase was extracted with EtOAc several times. Collected organic phases were dried with Na2SU4, filtered and evaporated to dryness affording 600 mg of the title compound. 1 H-NMR (400 MHz), delta (ppm, DMSO-de): 1.42 (s, 9H) 1.73 – 1.87 (m, 2H) 1.96 – 2.03 (m, 2H) 2.82 – 2.99 (m, 2H) 4.04 (d, J=12.93 Hz, 2H) 4.34 – 4.47 (m, 1H) 7.81 (s, 1H) 8.29 (s, 1H) 12.26 (br. s., 1H)

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; NERVIANO MEDICAL SCIENCES S.r.l.; MENICHINCHERI, Maria; BERTRAND, Jay, Aaron; MARCHIONNI, Chiara; NESI, Marcella; ORSINI, Paolo; PANZERI, Achille; WO2010/69966; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, 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 37622-90-5, Recommanded Product: Ethyl 4-pyrazolecarboxylate

A mixture of 1H-pyrazole-4-carboxylic acid ethyl ester (5.0 g, 35.7 mmol), PIVIBC1 (6.2 g, 39.3 mmol) and K2C03 (7.4 g, 53.6 mmol) in MeCN(100 mL) was refluxed for 16 hrs. Excessive K2C03 was removed by filtration and the filtrate was concentrated to dryness. The residue was purified by silica gel column (PE/EA = 5/1) to give 1-(4-methoxy-benzyl)-1H-pyrazole- 4-carboxylic acid ethyl ester (9.5 g, yield: >100%) as a colorless oil.

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:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 37622-90-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 37622-90-5 name is Ethyl 4-pyrazolecarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

292.1 (1H-pyrazol-4-yl)-methanol To a suspension of LiAlH4 (5.3 g) in dry THF (100 mL) in a round-bottomed flask, under inert atmosphere (N2), was added portionwise ethyl pyrazole-4-carboxylate (10.0 g) at rt. The reaction mixture was stirred at rt overnight and then poured into a sat. aq. Rochelle salt solution. The mixture was stirred at rt for 3 h and diluted with EA. The layers were separated and the aq. layer was extracted with EA (3*). The combined org. layers were dried over MgSO4, filtered and concentrated under reduced pressure. The title compound was obtained, after drying, as a white solid (5.2 g; 76% yield). 1H NMR (d6-DMSO) delta: 12.60 (s, 1H); 7.50 (s, 2H); 4.77 (br. s, 1H); 4.38 (br. s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-pyrazolecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Bur, Daniel; Gude, Markus; Hubschwerlen, Christian; Panchaud, Philippe; US2013/96119; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 37622-90-5,Some common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, molecular formula is C6H8N2O2, 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.

Under anhydrous condition, to a solution of ethyl 4-pyrazolecarboxylate (600 mg) in DMF (21ml, c=0.1 molL-1) cooled by an ice bath, NaH (in mineral oil 60%, 225 mg, 1.3 equiv.) was added in 3 portions (over 5 minutes). The mixture was stirred for 15 minutes, then methyl iodide (410 muL, 1.2 equiv.) was added. The ice bath was removed and the reaction was stirred at room temperature for 1 Hrs. The mixture was hydrolysed with a saturated aqueous solution of NaHCO3 (200 ml) and extracted twice with EtOAc (2*250 ml). The organic layers were combined, washed with brine (400 ml), dried over MgSO4 and concentrated. Purification by flash-chromatography (AcOEt in cyclohexane, 5 to 100%) afforded compound 107 as a colourless oil in 90% yield. 1H-NMR (400 MHz, DMSO): 1.26 (t, J 7.1 Hz, 3H, O-CHrCH3); 1.38 (t, J 7.3 Hz, 3H, N-CHrCH3); 4.17 (q, J 7.3 Hz, 2H, N-CH2-CH3); 4.21 (q, J 7.1 Hz, 2H, O-CH2-CH3); 7.84 (s, 1H, Ar);8.33 (s, 1H, Ar). M/Z (M+H)+ = 169.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-pyrazolecarboxylate, its application will become more common.

Reference:
Patent; DOMAIN THERAPEUTICS; MAYER, Stanislas; SCHANN, Stephan; WO2013/174822; (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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H8N2O2

NaH (80% in oil, 130 mg, 4.3 mmol, 1 .5 eq.) was added to 4-ethoxycarbonyl-1 H-pyrazole (400 mg, 2.86 mmol, 1 eq.) in THF (8 ml_), and the mixture stirred at r.t. for 30 min. SEMCI (556 muIota_, 3.14 mmol, 1 .1 eq.) was added and the reaction stirred at r.t. for 18 h. The mixture was partitioned between EtOAc (2 x 30 ml_) and water (20 ml_), the organic layers dried (MgS04) and the solvent removed in vacuo. The residue was purified by MPLC on silica with gradient elution from 5-20% EtOAc/petrol to give the title compound as a clear oil (657 mg, 85%); HRMS found 271 .1468 MH+

The synthetic route of 37622-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 37622-90-5, These common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, its 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.

Reference Example 1 ethyl 3,5-dibromo-1H-pyrazole-4-carboxylate (0885) (0886) To a mixed solution of ethyl 1H-pyrazole-4-carboxylate (31.0 g), sodium acetate (118 g), ethanol (200 mL) and water (300 mL) was added bromine (141 g), and the mixture was stirred at room temperature for 10 hr. To the reaction mixture was added sodium thiosulfate (175 g), and the solvent was evaporated under reduced pressure. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (65.1 g). MS (ESI+): [M+H]+ 296.7

Statistics shows that Ethyl 4-pyrazolecarboxylate is playing an increasingly important role. we look forward to future research findings about 37622-90-5.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 37622-90-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 37622-90-5 as follows.

To a solution of 20 (14.0 g, 100 mmol) and NaOAc (32.8 g,400 mmol) in EtOH/H2O (200 mL, v/v, 2/3) was added Br2 (39.95 g,250 mmol) at room temperature. The mixture was stirred at room temperature for 10 h. After addition of Na2S2O3 (31.62 g, 200 mmol)was added and the resulting mixture was then concentrated to afford the crude product, the mixture was poured into H2O at room temperature and was extracted with EtOAc. The organic layer was separated,washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 21 (26.6 g,92%) as a pale yellow solid. MS (ESI) m/z: 296.7 [M+H]+.

According to the analysis of related databases, 37622-90-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yin, Yuan; Chen, Cheng-Juan; Yu, Ru-Nan; Shu, Lei; Zhang, Tian-Tai; Zhang, Da-Yong; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1562 – 1576;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 37622-90-5, 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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

l-(Chloromethyl)-4-methoxybenzene (157 mmol, 24.5 g) and K2CO3 (39.43 g, 285.71 mmol) were added to a solution of ethyl lH-pyrazole-4- carboxylate (143 mmol, 20.0 g) in acetonitrile (150 mL). The resulting mixture was stirred under reflux for 5 h. After cooling to rt, the mixture was filtered and concentrated in vacuum. The residue was purified by flash chromatography over silica gel using EtOAc/PE ( 1 :20 to -1 :5) as eluent to afford ethyl l-(4-methoxybenzyl)-lH- pyrazole-4-carboxylate ( 126.7 mmol, 33 g, 89%) as an off-white solid. LC-MS: m/z ES = 261.

The synthetic route of Ethyl 4-pyrazolecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADDEX PHARMA S.A.; BOLEA, Christelle; CELANIRE, Sylvain; BOUDOU, Cedric; TANG, Lam; ROCHER, Jean-Philippe; LIVERTON, Nigel, J.; WO2012/9009; (2012); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics