Day: June 10, 2021

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5071-61-4, name is 5-Phenyl-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H8N2O2

A solution of acid 4 (0.09 g, 0.47 mmol) in dry DMF (2 mL) treated sequentially with amine (5a-i, 6a-e and 7a-h; 0.517 mmol)and triethylamine (0.94 mmol) was stirred under a N2 atmosphere for 15 min, later TBTU (0.56 mmol) was added and reaction mixture refluxed for 4-10 h. The reaction mixture was quenched with aq satd NH4Cl solution (10 mL). After 10 min, it was diluted withCHCl3 (2 10 mL) and washed with water (10 mL), NaHCO3 solution(10 mL) and brine (10 mL). The organic layers were dried over anhydrous sodium sulfate, evaporated and the residue purified by column chromatography using 30% ethyl acetate in pet. ether to afford corresponding amides 8a-i, 9a-e and 10a-h.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5071-61-4.

Reference:
Article; Doma, Anuradha; Kulkarni, Ravindra; Palakodety, Radhakrishna; Sastry, G. Narahari; Sridhara, Janardhan; Garlapati, Achaiah; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 6209 – 6219;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, 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. Computed Properties of C4H4N2O

To a 50-mL round-bottom flask was placed a solution of [( 1 s,3s)-3-(3-pheny 1- 1 ,2-oxazole-5-amido)cyclobuty l]methy 1 4-methylbenzene- 1 -sulfonate ( 1 g, 2.34 mmol, 1.00 equiv) in DMF (15 mL) then Cs2C03 (1.5 g, 4.60 mmol, 2.00 equiv) and lH-pyrazole-4-carbaldehyde (338 mg, 3.52 mmol, 1.50 equiv) were added. The resulting solution was stirred for 3 h at 100°C then the solids were removed by filtration. The crude product was purified by Flash-Prep-HPLC (CombiFlash-1 : Column, C18 silica gel; mobile phase, X: H20 (0.5percent NFUHCC ), Y: ACN, X/Y=90/10 increasing to X/Y=5/95 within 40 min; Detector, UV 254 nm) affording 460 mg (56percent) of 3-phenyl-N-[(l s,3s)-3-[(4-formyl-lH- pyrazol-l-yl)methyl]cyclobutyl]-l,2-oxazole-5-carboxamide as a yellow solid. LCMS (ES, m/z): [M+H]+ = 351.1.

The synthetic route of 35344-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (194 pag.)WO2016/105485; (2016); A2;,
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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: pyrazoles-derivatives

2D (3.5 g, 16.7 mmol) was dissolved in tetrahydrofuran (35 mL)Cooled to 0 C,60% sodium hydride (1.0 g, 25.4 mmol) was added,After reaction for 30 minutes, methylsulfonyl chloride (2.9 g, 25.4 mmol) was added and reacted for 1 hour.The reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (50 mL x 2). The organic layers were combined and the organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / Ethyl acetate (v / v) = 1: 1) to give 2E as a white solid (2.1 g, yield 44%).

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; ZHANG, CHEN; FAN, JIANG; LEI, MING; WEI, YONG-GANG; (61 pag.)TW2017/8223; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 176969-34-9, 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. 176969-34-9 name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, 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.

General procedure: Under nitrogen atmosphere, carboxylic acid II (3mmol), EDCI (3.3 mmol), HOBT (3.3 mmol)and Et3N (1.8 mmol) were placed in a three-necked flask with 40 mL CH2Cl2, and stirred for 2 hat 0 C; then, compound I (2.4 mmol) was added to the flask and allowed to react for 3 h at 0 C.The reaction was monitored by thin-layer chromatography (TLC) (all reactions could be completed in3 h) and, on completion of the reaction, the mixture was washed with saturated NaHCO3 solutionand water, respectively. Then, it was dried over anhydrous Na2SO4, filtered and evaporated onrotavapor in vacuum. Subsequently, crude products III-1-III-18 were purified by silica gel columnchromatography [V (CH2Cl2): V (EA) = 3:1] and crude products III-19-III-36 were purified by silicagel column chromatography [V (PE): V (EA) = 3:1]. Finally, products were recrystallized with thedichloromethane/petroleum ether to obtain pure target compounds.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Shen; Meng, Siqi; Xie, Yong; Yang, Yonggui; Zhang, Yumeng; He, Lu; Wang, Kai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Li, Xinghai; Molecules; vol. 24; 14; (2019);,
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. 1018446-95-1, name is tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, A new synthetic method of this compound is introduced below., Formula: C8H13N3O2

(C) 2-(2-(2-(2-(1H-Pyrazol-4-ylamino)-5-chloropyrimidin-4-yI)ethyl)phenyl)propanamide (35)A solution of 2-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)propanamide A30 (0.10 g, 0.31 mmol) and tert-butyl 4-amino-i H-pyrazole-1-carboxylate (0.17 g, 0.93 mmol) was heated in MeOH:water (10:1, 5 mL) at 90 00 for 18 hours. The solvents were removed in vacuo and the crude residue was purified by silica gel columnchromatography (Combiflash Rf, 0-15% MeOH in DCM). The purified fractions were combined, the solvent was removed in vacuo and the solid was sonicated in cyclohexane and filtered. The residue was dried in vacuo to give the title compound 35as a light yellow solid (0.060g, 52%). 1H NMR (300 MHz, d6-DMSO) O i.34(d, J=7.04 Hz, 3H), 2.92-3.11 (m, 4H), 3.86 (q, J= 7.04 Hz, 1H), 6.85 (brs, 1H), 7.13-7.25(m, 4H), 7.36-7.44 (m, 1H), 7.57-87 (m, 2H), 8.37 (5, 1H), 9.63 (5, 1H). LCMS-C: rt4.72 mm; m/z 371 [M+H].

The synthetic route of 1018446-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; HEMLEY, Catherine Fae; LUNNISS, Gillian Elizabeth; CAMERINO, Michelle Ang; GANAME, Danny; STUPPLE, Paul Anthony; LESSENE, Romina; KERSTEN, Wilhelmus Johannes Antonius; HARVEY, Andrew John; HOLMES, Ian Peter; WO2014/26243; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 5334-40-7 as follows. Quality Control of 4-Nitro-1H-pyrazole-3-carboxylic acid

Step 12-(4-Nitro- 1 H-pvrazo 1-3 -yl)-benzothiazoleTo a solution of4-nitro-1H-pyrazole-3-carboxylic acid (5 g, 31.8 mmol) in THF (40 mL) was added DMF (0.25 mL, 3.19 mmol) and oxalyl chloride (4.1 mL, 47.8 mmol). The mixture wasstirred at room temperature for 1 h and then concentrated under reduced pressure. The crude material was redissolved in NMP (40 mL) and 2-amino-beiizenethiol (4.0 mL, 31.8 mmol) was added. This mixture was heated at 100 °C for 1 h, at which point water (100 mL) was added and the aqueous phase extracted with ethyl acetate (3 x 25 mL). The combined organic layers were 42dried (Na2SO4), concentrated under reduced pressure, and purified by chromatography (silica, EtOAc / hexanes) to give 2-(4-nitro- 1 H-pyrazol-3 -yl)-benzothiazo le as a light yellow solid (4.8 g, 61 percent). MS (El/Cl) m/z: 245.0 [M – H].

According to the analysis of related databases, 5334-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BHAGIRATH, Niala; DOMINIQUE, Romyr; KENNEDY-SMITH, Joshua; LUCAS, Matthew C.; PADILLA, Fernando; WO2014/64134; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 25016-20-0, The chemical industry reduces the impact on the environment during synthesis 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, I believe this compound will play a more active role in future production and life.

Acid R2a (9.3 mg, 0.074 mmol) is dissolved in DCM (2 mL), then TEA (41 mu, 0.295 mmol) is added followed by TBTU (21.7 mg, 0.068 mmol). This solution is stirred for 15 mins, after which the amine hydrochloride Ce (50 mg, 0.059 mmol) is added. The resulting solution is stirred at RT for 16 h and then concentrated. The residual is dissolved in DMSO. The resulting solution is filtered through a Millex filter and purified by prep HPLC (Ammonium formate/MeOH). The pure fractions are combined, concentrated redissolved in MeCN and water, frozen and lyophilized to provide compound 1015.FIA M.S.(electrospray) : 804.5 (M-H)” Retention time (min): 5.2 min1H NMR (400 MHz,DMSO-d6): delta 9.57 (s, 1 H) , 7.76 (d, 1 H, J = 2.4 Hz), 7.67 (bs, 1 H). 7.64 (d, 1 H, J = 9 Hz), 6.88 (d, 1 H, J = 9 Hz), 6.59 (d, 1 H, J = 2.1 Hz), 6.24 (s, 1 H), 5.47 (S, 1 H, J = 6.1 Hz), 5.41-5.31 (m, 3H) 4.81-4.73 (m, 1 H), 4.46 (dd, 1 H, J = 7.8, 7.6 Hz), 4.30-4.13 (m, 2H) 3.90 (s, 3H), 2.46-2.41 (m, 2H), 2.38 (s, 3H), 2.01- 1.69 (m, 4H), 1.59-1.53 (m, 3H), 1.48-1.33 (m, 15H), 1.24-1.12 (m, 4H), 0.64- 0.60(m, 2H)

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, 1-Methyl-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET, Montse; BORDELEAU , Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63501; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5744-80-9, A common heterocyclic compound, 5744-80-9, name is 3-Bromo-1,5-dimethyl-1H-pyrazole, molecular formula is C5H7BrN2, 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.

Example 173 3-amino-5-(dicyclopropylmethyl)-7-(1,5-dimethyl-1H-pyrazol-3-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one (0879) A mixture of 3-amino-7-bromo-5-(dicyclopropylmethyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one (300 mg) obtained in Example 78, Step C, 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (283 mg), tetrakis(triphenylphosphine)palladium(0) (107 mg), potassium acetate (182 mg) and N,N-dimethylacetamide (4 mL) was stirred under an argon atmosphere at 110C for 4 hr. The reaction mixture was cooled to room temperature, 3-bromo-1,5-dimethyl-1H-pyrazole (195 mg), aqueous sodium carbonate solution (2 M, 0.928 mL) and tetrakis(triphenylphosphine)palladium(0) (107 mg) were added. Under an argon atmosphere, the reaction mixture was stirred at 130C for 5 hr. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate) and further purified by silica gel chromatography (diol silica gel, hexane/ethyl acetate). The obtained solid was crystallized from ethyl acetate/diisopropyl ether to give the title compound (104 mg).

The synthetic route of 5744-80-9 has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 55864-87-4, 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. 55864-87-4 name is Ethyl 4-nitro-1H-pyrazole-3-carboxylate, 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.

A mixture of 4-nitro-lH-pyrazole-3-carboxylic acid ethyl ester (6.40 g, 34.6 mmol) and 10% Pd/C (650 mg) in EtOH (150ml) was stirred under an atmosphere of hydrogen for 20 h. The mixture was filtered through a plug of Celite, reduced in vacuo and dried through azeotrope with toluene to afford 4-amino-lH-pyrazole-3- carboxylic acid ethyl ester as a pink solid (5.28 g, 98%). (1H NMR (400 MHz, DMSOd6) delta 12.7 (s, IH)5 7.1 (s, IH), 4.8 (s, 2H)5 4.3 (q, 2H), 1.3 (t, 3H)).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-nitro-1H-pyrazole-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/70198; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 152120-54-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Diisopropyl azodicarboxylate (DIAD, 1.5 equiv) was added dropwise to a stirred solution of alcohol 1a-g (1-2 equiv), N,N?-bis-tert-butoxycarbonylpyrazole-1H-carboxamidine 2 (2.5 mmol, 1 equiv), and Ph3P (1.5 equiv) in THF (7 mL) at 0 C. The reaction mixture was stirred overnight (16 h) at r.t., concentrated in vacuum, and the residue was purified by flash column chromatography on silica gel (10-25% EtOAc-hexane) to give the N-alkylated guanylating agent 3a-g as colorless oils.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Tommasi, Sara; Zanato, Chiara; Carabeo, Rey; Mangoni, Arduino A.; Dall’Angelo, Sergio; Zanda, Matteo; Synthesis; vol. 47; 19; (2015); p. 3067 – 3078;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics