Day: May 18, 2021

Application of 15001-11-3, These common heterocyclic compound, 15001-11-3, name is Ethyl 5-amino-1-(p-tolyl)-1H-pyrazole-4-carboxylate, 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.

General procedure: To ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate (2a, 1.60 g, 6.92 mmol) in 4N HCl in 1,4-dioxane (35 mL) at room temperature was added methyl cyanoformate (1.77 g, 20.8 mmol). The mixture was stirred at 100 C for 14 h and was cooled to room temperature. After 1,4-dioxane was removed in vacuo and the residue was partitioned between methylene chloride and water. The organic layer was dried over magnesium sulfate and was evaporated in vacuo. The residue was chromatographed on a silica gel column with a mixture of methylene chloride and ethyl acetate (7:1) to give the desired product 3a (1.47 g, 78 %).

The synthetic route of 15001-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Heo, Yun-Jeong; Jeon, Moon-Kook; Tetrahedron; vol. 73; 40; (2017); p. 5959 – 5973;,
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. 96450-53-2, name is 1-(2-Chloroethyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H7ClN2

1 -(2-Chloroethyl)-1 1H-pyrazole was prepared by reacting pyrazole with 1 – bromo-2-chloroethane. Lambda/-[1 -(Fluoromethyl)cyclopropyl]-3-[(1 -methylpyrazol-4-yl)methyl]- 2,4-dioxo-1 H-quinazoline-6-sulfonamide (100 mg, 0.260 mmol), 1 -(2-chloroethyl)-1 H- pyrazole (37 mg, 0.286 mmol) and potassium carbonate (43 mg, 0.312 mmol) in DMF was conventionally heated to 70 C for 4 h. Usual work-up afforded the desired product (7 mg, 0.014 mmol, 5.4%) as a white powder.

According to the analysis of related databases, 96450-53-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan; WASZKOWYCZ, Bohdan; HUTTON, Colin; WADDELL, Ian; HITCHIN, James R.; SMITH, Kate Mary; HAMILTON, Niall M.; (497 pag.)WO2016/92326; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 611239-23-7, name is tert-Butyl 1H-pyrazole-4-carboxylate, 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. Computed Properties of C8H12N2O2

Synthetic Method B; Alternative procedure 2; Example 45: 1-(ff (2S)-4-(3. 4-Dichlorobenzvl) morpholin-2- vlmethvllcarbamovl) methvl)-1 H-pvrazole-4-carboxylic acid tert-butvl ester Potassium tert-butoxide (0.045g) was added to a solution 1 H-pyrazole-4- carboxylic acid ter-butyl ester (0.055g) in N, N-dimethylformamide (1ml). The mixture was stirred at 20C for 0.75h before a solution of Description 9 (0.099g) in N, N-dimethylformamide (0. 5ml) was added to it. The mixture was stirred at 20C for 2h then left to stand overnight. The mixture was diluted with ethyl acetate (35ml), washed with 1 M aqueous sodium bicarbonate solution (30mi) and water (30ml), dried over sodium sulphate and concentrated in vacuo to give a gum. The gum was purified on a 20g SPE cartridge, eluting initially with ethyl acetate and then with a (100: 1) mixture of ethyl acetate/methanol. The product containg fractions were evaporated in vacuo to give the title compound (0.032g) as a pale brown gum. LCMS Rt 2.62 min, m/z483 [MX]

The synthetic route of tert-Butyl 1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2003/82862; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 741717-59-9, name is 2-(1-Pyrazolyl)benzyl Alcohol, 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 741717-59-9, HPLC of Formula: C10H10N2O

To a solution of DMSO (670 mg, 8.56 mmol) in anhydrous DCM was added oxalyl chloride (220 mg, 1.73 mmol) at -70 C under nitrogen atmosphere and the mixture was stirred for 30 mm. A solution of X4-095-2 (300 mg, 1.72 mmol) in DCM was then added and stirring was continued at the same temperature for 30 mm before Et3N (1.4 g, 13.9 mmol) was added. After stirring for 20 mm at 0 C the mixture was diluted with DCM (50 ml), and then washed with water (10 ml), 1 M HC1 (10 mL), saturated aq. NaHCO3 solution (10 mL) and brine (10 mL). The organic phase was dried over Na2SO4 and evaporated in vacuo. The residual material was purified by silica gel column chromatography to give X4-164-4b (200 mg, 67%) as a white solid. LCMS (Agilent LCMS 1200-6110, Column: Waters X-Bridge C18 (50 mm*4.6 mm*3.5 jim); Column Temperature: 40 C; Flow Rate: 2.0 mL/min; Mobile Phase: from 95% [water + 0.05% TFA] and 5% [CH3CN + 0.05% TFA] to 0% [water + 0.05% TFA] and 100% [CH3CN + 0.05 % TFA] in 1.6 mm, then under this condition for 1.4 mm, finally changed to 95% [water + 0.05% TFA] and 5% [CH3CN + 0.05% TFA] in 0.05 mm and under this condition for 0.7 mm) Purity: 92%. Rt = 1.495 mm; MS Calcd.: 172.1; MS Found: 173.1 [M + H].

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, 2-(1-Pyrazolyl)benzyl Alcohol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; X4 PHARMACEUTICALS, INC.; BOURQUE, Elyse Marie Josee; SKERLJ, Renato; (190 pag.)WO2017/223243; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 15001-11-3, 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 15001-11-3 as follows.

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

According to the analysis of related databases, 15001-11-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
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. 1000896-40-1, name is 5-(Benzyloxy)-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., name: 5-(Benzyloxy)-1H-pyrazol-3-amine

There was dissolved, in ethanol (30 mL), 5-benzyloxy-2H-pyrazol-3-yl-amine (1.52 g, 8.03 mM) and then a methanol solution of sodium methoxide (5.03M, 3.51 mL, 17.7 mM) and diethyl malonate (1.47 mL, 9.64 mM) were added to the solution. This reaction liquid was stirred for 2 hours while refluxing the same with heating. This reaction mixture was filtered and the resulting solid was washed with diethyl ether. After the addition of phosphoryl chloride (10 mL) to the resulting solid with ice-cooling, the resulting suspension was stirred for 3 hours while refluxing the same with heating. The phosphoryl chloride was distilled off from this reaction liquid, ethanol was then added to the residue thus obtained with ice-cooling and the mixture was stirred for 15 minutes. After the concentration of this reaction liquid, the concentrate was purified by the silica gel column chromatography (ethyl acetate/hexane=1:100) to thus give the title compound (167 mg, overall yield of these two steps: 7%). 1H-NMR (300 MHz, CDCl3): delta 5.41 (s, 2H), 6.12 (s, 1H), 6.83 (s, 1H), 7.34-7.40 (m, 3H), 7.48-7.51 (m, 2H); MS (ESI) m/z 294 (M+H)+.

According to the analysis of related databases, 1000896-40-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AJINOMOTO CO., INC.; US2011/294781; (2011); 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. 796729-03-8, name is 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid

Example 133N-((ls,4s)-4-(5-fluoro-2-(4′-(3-(piperazin-l-yl)propyl)biphenyl-3- yloxy)nicotinamido)cyclohexyl)-5,6-dihydro-4H-pyrrolo[l,2-b]pyrazole-2-carboxamide To a solution of tert-butyl 4-(3-(3′-(3-((ls,4s)-4-aminocyclohexylcarbamoyl)-5-fluoropyridin- 2-yloxy)biphenyl-4-yl)propyl)piperazine-l-carboxylate (150 mg, 0.24 mmol) in acetonitrile (2 mL) was added 5,6-dihydro-4H-pyrrolo[l,2-b]pyrazole-2-carboxylic acid (36.1 mg, 0.24 mmol) and triethylamine (0.331 mL, 2.37 mmol). 1-Propanephosphonic acid cyclic anhydride, 1.57M solution in THF (0.159 mL, 0.25 mmol) was then added and the mixture stirred at RT for 1 h. The mixture was poured into sat NaHCO3 (aq) and the organics extracted into EtOAc (x2). The extractions were combined, dried (MgSO4) and evaporated to give a residue. This was dissolved in DCM (2mL) to which TFA (2mL) was added and the mixture stirred at RT for 20 min. The solvents were removed in vacuo and the residue dissolved in methanol and purified using reverse phase preparative chromatography using eluent = TFA(aq)/MeOH. The appropriate fractions were combined and evaporated to give a residue which on trituration with ether gave a solid. The solid was dried overnight under vacuum at 400C to give the title compound. Yield: 48 mg1H NMR (400 MHz, CD3OD) 5 8.45 (d, J= 7.2 Hz, IH), 8.11 (d, J= 3.1 Hz, IH), 8.05 (dd, J = 7.9, 3.1 Hz, IH), 7.51 (d, J= 8.2 Hz, 2H), 7.47 (d, J= 5.1 Hz, 2H), 7.40 – 7.39 (m, IH), 7.24 (d, J= 8.2 Hz, 2H), 7.15 – 7.12 (m, IH), 6.39 (s, IH), 4.14 – 4.07 (m, IH), 4.03 (t, J= 7.3 Hz, 2H), 3.99 – 3.92 (m, IH), 3.41 (t, J= 5.1 Hz, 4H), 3.24 – 3.19 (m, 4H), 2.95 – 2.90 (m, 2H), 2.87 (t, J= 7.3 Hz, 2H), 2.71 (t, J= 7.4 Hz, 2H), 2.61 – 2.53 (m, 2H), 2.04 – 1.95 (m, 2H), 1.87 – 1.77 (m, 6H), 1.73 – 1.64 (m, 2H). MS: [M+H]+=666 (calc=666) (MultiMode+)

The synthetic route of 796729-03-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); 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. 19959-77-4, name is 2-(5-Methyl-1H-pyrazol-3-yl)pyridine, A new synthetic method of this compound is introduced below., Computed Properties of C9H9N3

A 5mL methanol solution of L (0.2mmol, 31.8mg) and m-phthalic acid (0.2mmol, 33.2mg) was mixed with a 5mL methanol solution of Mn(HCOO)2·2H2O (0.1mmol, 14.5mg), and the resulting mixture was then stirred 15min to obtain a colorless solution. This colorless solution was filtered and left to evaporate for one week, giving rise to colorless stick-like crystals. The resulting crystals were washed with n-hexane 2?3 times, then dried in vacuum. Yield: 47.1mg (67%), M. p. > 300C. Anal. Calc. for C34H28MnN6O8 (FW, 703.56): C, 58.04; H, 4.01; N, 11.95. Found: C, 58.98; H, 4.73; N, 11.49%. Selected IR data (cm-1, KBr): 3256 (b, s), 3128 (m), 3073 (m), 2925 (m), 2883 (m), 1694 (s) (nu(C=O)), 1606 (m) (nu(C=N)), 1561 (s) (nu(C=C)), 1428 (m) (delta(CH3)), 1392 (s), 1296 (m) (nu(C-N)), 1161 (w), 777 (m), 733 (m), 689 (m).

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:
Article; Zhu, Guang-Zhou; Xing, Bei-Bei; Yang, Feng-Lei; Li, Xiu-Ling; Polyhedron; vol. 81; (2014); p. 705 – 714;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 575452-22-1, name is 1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole, molecular formula is C7H11IN2O, 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. COA of Formula: C7H11IN2O

General procedure: To a suspension of magnesium (1.3 equiv) in THF (for 1 mol of magnesium 700 mL of THF wereused), at the boiling temperature under argon atmosphere, ethyl bromide (1.4 equiv) was addeddropwise and left to stir at same temperature for one hour. Then the reaction mixture was cooleddown to given temperature and solution of starting pyrazole derivative 2a, 3a or 6a (1 equiv) inTHF (for 1 mol of pyrazole 350 mL of THF were used) was added dropwise at same temperature.After 1 hour of stirring at the same temperature dimethylformamide (1.5 equiv) was added to thereaction mixture dropwise and left to warm to room temperature overnight. Then saturated NH4Cl(5 equiv) solution in deionized water were added to the reaction mixture, organic layer wasseparated and NH4Cl solution was extracted with dichloromethane (for 1 mol of pyrazole 0.5 L ofdichloromethane were used) twice. Organic layers were combined, washed with deionized water(for 1 mol of pyrazole 0.5 L of water were used), dried with anhydrous Na2SO4 and evaporatedunder reduced pressure. Products were purified by distillation or column chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 575452-22-1, its application will become more common.

Reference:
Article; Mazeikaite, Rita; Sudzius, Jurgis; Urbelis, Gintaras; Labanauskas, Linas; ARKIVOC; vol. 2014; 6; (2014); p. 54 – 71;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 73387-52-7, name is 5-(4-Bromophenyl)-1-methyl-1H-pyrazole, 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 73387-52-7, Safety of 5-(4-Bromophenyl)-1-methyl-1H-pyrazole

Step 4: Preparation of 4-(3-{[4-(1-methyl-1H-pyrazol-5-yl)phenyl]thio]phenyl) tetrahydro-2H-pyran-4-carboxamide; Scale-Up Alternative; 4-{3-[(tri-isopropylsilyl)thio]phenyl}tetrahydro-2H-pyran-4-carboxamide (200 g, 0.51 moles), 5-(4-bromophenyl)-1-methyl-1H-pyrazole (126 g, 0.53 moles), and 2-methyltetrahydrofuran (2,000 mL, 10 mL/g of tips carboxamide) were put into the reactor and sparged with nitrogen while heating to 60 C. The sodium methoxide (244.0 mL, 1.07 moles, added as sodium methoxide in methanol solution 25% w/w) was added to the reactor and sparging was continued for another 30 minutes. PdCl2DPPF (3.7 g, 0.005 moles) was added to the reactor and the mixture was heated to 70 C. Once the amount of tips carboxamide was less than 1% of starting amount, the mixture was cooled to 0 C. The mixture was held at 0 C. for one hour. The mixture was filtered and the solid was washed with 2-methyltetrahydrofuran (3×2.5 mL/g). The solid was dried on the filter. The solid was returned to a clean reactor and triturated with water (2,000 mL, 10 mL/g) for two hours at 20 C. The mixture was filtered and the solid was washed with water (2,000 mL, 2×5 mL/g). The solid was dried on the filter. The solid was returned to a clean reactor with the Si-thiol (90.0 g, 0.5 g/g) and THF (about 12.8 L, 70 mL/g). The mixture was heated to 60-65 C. and held for two hours. The mixture was cooled to 25 C. and filtered. The Si-thiol was washed with THF (about 0.9 L, 5 mL/g). The solution was distilled to a concentration of 10 mL/g. The mixture was cooled to 25 C. and hexanes (422.5 mL, 5 mL/g) was added. The mixture was filtered and the solid was washed with hexanes (422.5 mL, 5 mL/g). The solid was dried in a vacuum oven at 70 C.For 2-methyltetrahydrofuran and water, mL/g are referred to grams of tips carboxamide. For Si-thiol, tetrahydrofuran and hexanes, mL/g are referred to grams of title compound.

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; Graneto, Mathew J.; Maddux, Todd M.; Masferrer, Jaime L.; US2008/125474; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics