Day: May 26, 2021

Application of 10010-93-2, A common heterocyclic compound, 10010-93-2, name is 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, molecular formula is C5H5F3N2, 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 128: Preparation of l,5-dimethyl-3-trifluoromethyl-l//-pyrazoleTo a solution of 5-methyl-3-trifluoromethyl-lH-pyrazole (4.13 g, 27.5 mmol) (Example 127) in tetrahydrofuran (60 ml), was added slowly at room temperature potassium tert-butoxide (6.18 g, 55 mmol) and 15 minutes later methyl iodide (3.43 ml, 0 55 mmol). The reaction mixture was stirred for lhour before adding more potassium tert- butoxide (3.09 g, 27.5 mmol). After 30 minutes the reaction mixture was quenched by addition of water and extracted with dichloromethane. The organic extract was dried over magnesium sulfate and concentrated to give l,5-dimethyl-3-trifluoromethyl-lH-pyrazole (3.55 g) which was used in the next step without further purification. 5 1H-NMR (400 MHz, CDCl3): 2.30 (s, 3H, Me)5 3.82 (s, 3H, Me), 6.28 (s, IH, CH) ppm.

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; SYNGENTA LIMITED; WO2007/71900; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 110860-60-1, name is Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C6H9N3O2, 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. SDS of cas: 110860-60-1

Synthesis of D-77; 1 g of compound (18) is added to 10 ml of phosphoric acid, and the mixture is heated to 30C to dissolve. This solution is cooled with ice and, while keeping the temperature of the solution at -5 to 0C, 0.46 g of sodium nitrite is added thereto, followed by stirring for 1 hour to obtain a diazonium salt solution. Separately, 0.93 g of the compound (17) is dissolved in 10 ml of methanol, and the aforesaid diazonium salt solution is added thereto at 8C or lower. At the time of completion of the addition, the ice bath is removed, followed by stirring the mixture for 2 hours. The reaction solution is added to 30 ml of acetonitrile, and the mixture is stirred at room temperature for 30 minutes. Crystals precipitated are collected by filtration, and spray-washed with 20 ml of acetonitrile. The crystals are added, without drying, to 50 ml of a 1% sodium hydrogencarbonate aqueous solution, and the mixture is stirred for 1 hour. The crystals are collected by filtration, and spray-washed with a sufficient amount of water. The thus-obtained crystals are added, without drying, to a solution composed of 15 ml of dimethylacetamide (DMAc) and 25 ml of water and, after stirring at 80C for 1 hour, the mixture is stirred at room temperature for 2 hours. Crystals precipitated are collected by filtration and spray-washed with 30 ml of a mixture of DMAc/water (=1/2). The thus-obtained crystals are dried to obtain 1.1 g of compound D-77 of the invention. Yield: 55.0%. Infrared absorption chart of compound D-77 is shown in Fig. 27. IR charts of typical compounds synthesized in Synthesis Examples 1 to 8 and those synthesized in the similar manner are shown in Figs. 1 to 27.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 110860-60-1, its application will become more common.

Reference:
Patent; FUJIFILM Corporation; EP2253674; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 118430-73-2, 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. 118430-73-2, name is 3-(tert-Butyl)-1-methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of 3-tert-butyl-l -methyl- lNo.-pyrazol-5-amine (792 mg), phenyl 3-ethynylphenylcarbamate (Intermediate 13) (1.19 g) and triethylamine (1.4 mL) in THF (30 5 mL) was heated to 60C for 24 hours. Additional triethylamine (0.5 mL) and 3-tert-bu.tyl-l-methyl-lNo.-pyrazol-5-amine (200 mg) were added and the mixture heated for a further 4 hours and concentrated in vacua. The residue was partitioned between DCM and 50% saturated aqueous Na2COs solution. The aquous phase was extracted with DCM and the combined organics washed with 50% saturated aqueous Na2CO3 solution, water and brine and10 concentrated in vacua. Purification by flash chromatography on silica using 0-5% MeOH in DCM as eluent, followed by 20-50% EtOAc in DCM gave the title compound as a white solid (725 mg, 49%)..H NMR (CDC13) 1.30 (s, 9H), 3.08 (s, 1H), 3.75 (s, 3H), 6.11 (s, ), 6.63 (s, 1H), 6.84 (s,1H), 7.19-7.30 (m, 2H), 7.40 (dt, 1H), 7.46 (s, );15 MSm/eMH+297

The synthetic route of 3-(tert-Butyl)-1-methyl-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/60969; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

30.8g (0.151mol)3-Fluoroalkyl-1-methylpyrazole-4-carboxylic acid ethyl ester (DFMPA) was put into the reaction flask, 100 g of water, 6.7 g of sodium hydroxide were added, and the reaction was stirred at 70 C for 2 hours. After the reaction was completed, Add hydrochloric acid dropwise to neutralize to pH 2, cool to 10 C, filter, wash with a little cold water, and dry to obtain 3-fluoroalkyl-1-methyl-1H-pyrazole-4-carboxylic acid (DFMPA) (such as (Expression V) 25.2 g, 95% yield, 99% purity by HPLC.

According to the analysis of related databases, 141573-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Suqian Kelaibo Biochemical Co., Ltd.; Wang Mingchun; Li Qingyi; (11 pag.)CN110577503; (2019); A;,
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. 1613191-73-3, name is Allyl 3,5-diamino-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C7H10N4O2

[0464] To a suspension ofallyl3,5-diamino-1H-pyrazole-4-carboxylate 3 (1 g, 5.489 mmol) in DMF (5 mL) was added(Z)-2-chloro-3 -dimethy amino-prop-2-eny lidene ]-dimethy ammoniumhexafluorophosphate (1.683 g, 5.489 mmol), followedby triethylamine (722.1 mg, 994.6 f.LL, 7.136 mmol).The reaction mixture was heated to 60 C. for 4 hr. duringwhich time a solid slowly precipitated out of solution. Thebrown suspension was allowed to cool down to RT. The solidwas filtered, washed with water and dried under vacuum togive allyl 2-amino-6-chloro-pyrazolo[1,5-a]pyrimidine-3-carboxylate 4b as a brown solid (1.092 g, 72% yield).Step 2: 2-amino-6-chloro-pyrazolo[1 ,5-a ]pyrimidine-3

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; Charrier, Jean-Damien; Davis, Christopher John; Fraysse, Damien; Etxebarria I Jardi, Gorka; Pegg, Simon; Pierard, Francoise; Pinder, Joanne; Studley, John; Zwicker, Carl; Sanghvi, Tapan; Waldo, Michael; Medek, Ales; Shaw, David Matthew; Panesar, Maninder; Zhang, Yuegang; Alem, Naziha; US2015/158872; (2015); 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. 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate

3-(6-(5-Methyl-lH-pyrazol-3-ylamino)pyrazin-2- ylamino)benzonitrile. 3-(6-chloropyrazin-2-ylamino)benzonitrile (0.32 g, 1.39 mmol), tert-butyl 3-amino-5-methyl-lH-pyrazole-l-carboxylate (0.3 g, 1.53 mmol), palladium acetate (31 mg, 10 mol%), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (160 mg, 20 mol%), and potassium carbonate (0.96g, 6.95 mmol) were suspended in dioxane (8 mL). The mixture was stirred in a sealed flask at 9O0C for 1 hour. The reaction mixture was cooled, diluted with ethyl acetate (50 mL), washed with water (50 mL), and then with brine (30 mL). The organic layer was dried (sodium sulfate), filtered, and concentrated. The crude residue was dissolved in chloroform (20 mL) and 4N HCl in dioxane (3 mL) was added. The mixture was stirred at room temperature for 2 hours and the solvent evaporated. The crude product was purified by reverse-phase preparative HPLC (10-70% acetonitrile + 0.1% TFA in H2O + 0.1% TFA, over 30 min). Fractions containing product were condensed and neutralized on a Strata-XC ion exchange column (Phenomenex). The product was loaded and the column washed successively with water, acetonitrile, and methanol. The product was released with 5% ammonium hydroxide in methanol and product containing eluent was concentrated under reduced pressure and dried to give the title compound as a white solid (0.29g, 72% yield); m.p. 260-262C; 1H NMR (300 MHz, DMSCW6) delta 11.89 (br s, IH), 9.50 (s, IH), 9.38 (s, IH), 8.34 (s, IH), 7.89 (s, IH), 7.69 (dd, J, = 8.4 Hz, J2= 1.2 Hz, IH), 7.52 (s, IH), 7.43 (t, J= 8.4 Hz, IH), 7.31 (d, J= 7.6 Hz, IH), 6.05 (s, IH), 2.21 (s, 3H); MS (ESI) MS (ESI) m/z 292.0 [M+ 1]+.

The synthetic route of 578008-32-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2009/89042; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 309740-49-6, 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. 309740-49-6 name is Methyl 1-methyl-4-nitro-1H-pyrazole-5-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.

General procedure: To a solution of 15a (3.57 g, 16.8 mmol) in MeOH (60 mL) wasadded Pd/C (50% wet, 0.178 g), and the mixture was stirred at room temperature for 2 h under hydrogen atmosphere. The insolublematerials were filtered off by using a pad of Celite, and the Celitewas washed with MeOH. The filtrate was concentrated in vacuo.The residue was diluted with EtOAc, washed with brine, dried overMgSO4, and filtered. The filtrate was concentrated in vacuo toafford 16a

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Article; Kojima, Takuto; Asano, Yasutomi; Kurasawa, Osamu; Hirata, Yasuhiro; Iwamura, Naoki; Wong, Tzu-Tshin; Saito, Bunnai; Tanaka, Yuta; Arai, Ryosuke; Yonemori, Kazuko; Miyamoto, Yasufumi; Sagiya, Yoji; Yaguchi, Masahiro; Shibata, Sachio; Mizutani, Akio; Sano, Osamu; Adachi, Ryutaro; Satomi, Yoshinori; Hirayama, Megumi; Aoyama, Kazunobu; Hiura, Yuto; Kiba, Atsushi; Kitamura, Shuji; Imamura, Shinichi; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2452 – 2465;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, 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. SDS of cas: 288148-34-5

te/f-Butyl (2-[1-(4-chlorophenyl)cyclobutyl]-2-{3-[(methylamino)methyl]phenyl}ethyl)carb- amate (35 mg, 0.082 mmol) was dissolved in dichloromethane (0.8 mL). 4-Dimethylamino- pyridine (10 mg, 0.082 mmol) and 1-methyl-1 H-pyrazole-4-sulfonyl chloride (16 mg, 0.09 mmol) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with ethyl acetate (20 ml) and washed with aqueous hydrochloric acid (1 N, 5 ml, twice) and sodium bicarbonate. The organic layer was dried (magnesium sulfate) and concentrated in vacuo. The crude product was purified by preparative thin layer chromatography (silica, ethyl acetate, n-heptane). Yield: 36 mg(0.063 mmol, 77%)ESI-MS [M-C02-isobutene+H+] = 473 Calculated for C29H37CIN4O4S = 572

The synthetic route of 1-Methyl-1H-pyrazole-4-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT GMBH & CO. KG; ABBOTT LABORATORIES; AMBERG, Wilhelm; OCHSE, Michael; LANGE, Udo; BEHL, Berthold; HORNBERGER, Wilfried; MEZLER, Mario; POHLKI, Frauke; TURNER, Sean; HUTCHINS, Charles; WO2012/20130; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 16034-48-3, A common heterocyclic compound, 16034-48-3, name is 1-Pyrazoleacetic Acid, molecular formula is C5H6N2O2, 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.

A solution of Example 1G and DIPEA (0.15 M and 0.43 M in DMA, respectively, 257 iL, 0.04 mmol Example 1G (1.0 equivalent) and 0.12 mmol DIPEA (3.0 equivalents)),HATU (0.2 M in DMA, 257 iL, 0.052 mmol, 1.3 equivalents), and 2-(1H-pyrazol-1-yl)acetic acid (0.40 M in DMA, 121 iL, 0.048 mmol, 1.2 equivalents) were aspirated from their respective source vials, mixed through a perfluoroalkoxy mixing tube (0.2 mm inner diameter), and loaded into an injection loop. The reaction segment was injected into the flow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mL internal volume) set at 100 C, andpassed through the reactor at 180 iL min1 (10 minute residence time). Upon exiting the reactor, the reaction was loaded directly into an injection loop and purified by preparative HPLC on a Phenomenex Luna C8(2) 5 tm boA AXIA column (50 mm x 21.2 mm). A gradient of acetonitrile (A) and 0.1 % ammonium acetate in water (B) was used, at a flow rate of 30 mL/min (0-0.5 mm 5 % A, 0.5-6.5 mm linear gradient 5-60 % A, 6.5-7.0 mm lineargradient 60-100 % A, 7.0-8.9 mm 100 % A, 8.9-9.0 mm linear gradient 100-5 % A, 9.0-10 mm 5 % A) to yield the title compound (7.33 mg, 39 % yield). ?H NMR (400 MHz, DMSOd 6/D20) oe 7.76 (d, J= 2.3 Hz, 1H), 7.60 – 7.45 (m, 4H), 7.37 – 7.28 (m, 1H), 7.07 – 6.87 (m, 3H), 6.31 (t, J= 2.1 Hz, 1H), 5.82 (s, 1H), 5.00 (s, 2H), 3.93 (q, J= 6.9 Hz, 2H), 3.36 (s, 3H),1.14 (t, J= 6.9 Hz, 3H). MS (ESI) mlz 481.1 (M+Hj.

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; ABBVIE INC.; SHEPPARD, George, S.; BOGDAN, Andrew; KATI, Warren, M.; PARK, Chang, H.; WANG, Le; MCDANIEL, Keith, F.; WO2015/89075; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 26621-44-3, A common heterocyclic compound, 26621-44-3, name is 3-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

Step B: To a stirred mixture of 3-nitro-lH-pyrazole (3.16 g, 27.9 mmol) in glacial acetic acid (20 mL) at 0 C was added fuming nitric acid (2.6 mL, 58.69 mmol) dropwise, followed by acetic anhydride (6.6 mL, 69.87 mmol). The mixture was stirred and allowed to warm to rt over 3 h, then poured into ice water (50 mL) and stirred for 20 h. The mixture was extracted with EtOAc combined organic layers were dried over MgS04, filtered and concentrated to dryness to afford 1,3- dinitro-lH-pyrazole (4.3 g, 97%). JH NMR (300 MHz, DMSO-t/6) delta 8.00 (br s, 1H), 6.44 (br s, 1H).

The synthetic route of 26621-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; FARAONI, Raffaella; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; SETTI, Eduardo; WO2012/30944; (2012); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics