Month: June 2021

Application of 55864-87-4, 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. 55864-87-4, name is Ethyl 4-nitro-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 2. 4-Amino-lH-pyrazole-3-carboxylic acid ethyl ester ; A mixture of 4-nitro-lH-pyrazole-3-carboxylic acid ethyl ester (6.40 g, 34.6 mmol, prepared analogous to Preparation I) and 10% Pd/C (650 mg) in EtOH (150ml) was stirred under an atmosphere of hydrogen for 20 hours. 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%). (1HNMR (400 MHz, DMSOd6) delta 12.7 (s, IH), 7.1 (s, IH), 4.8 (s, 2H), 4.3 (q, 2H), 1.3 (UH)).

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, Ethyl 4-nitro-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; NOVARTIS AG; WO2008/7123; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3524-32-1, 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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 3-methyl-1-phenyl-1H-pyrazol-5-amine (1 mmol, 173 mg) and acetophenone (1.5 mmol, 180 mg), CuI (10 mol %, 19 mg) and FeCl3.6H2O (10 mol %, 27 mg) were added in DMSO (2 mL) at 120C in a round-bottom flask equipped with a magnetic stirring bar and a reflux condenser. After completion of the reaction the organic mixture was extracted with ethyl acetate (3×50 mL) and then washed with brine solution. The organic fraction was dried with anhydrous sodium sulphate and concentrated in rotavapor under vacuum. The product was purified by column chromatography using silica gel (100-200 mesh, ethyl acetate/hexane as eluent).

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, 5-Amino-1,3-dimethylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Rastogi, Gaurav K.; Saikia, B-Shriya; Pahari, Pallab; Deb, Mohit L.; Baruah, Pranjal K.; Tetrahedron Letters; vol. 60; 17; (2019); p. 1189 – 1192;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

34605-66-8, name is 3-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole, 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. name: 3-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole

To 3-(2,5-Dimethyl-pyrrol-1-yl)-1-methyl-1H-pyrazole (4.5 g, 25.71 mmol) in dry THF (40 ml) at -78 C. was added n-BuLi (1.7M, 16.4 ml, 28.02 mmol). The reaction mixture was stirred for 2 h at -78 C. before CNBr (2.97 g, 28.02 mmol) dissolved in THF (5 ml) was added. The mixture was allowed to warm to rt, and stirred for an additional 2 h, after which ice-water was added and the aqueous mixture extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by column chromatography to give 5-Bromo-3-(2,5-dimethyl-pyrrol-1-yl)-1-methyl-1H-pyrazole (4.4 g, 68%).

The synthetic route of 34605-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (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. 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C4H5IN2

A degassed solution of 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpyridin-2(1H)-one (27 mg, 0.100 mmol), 3-iodo-1-methyl-1H-pyrazole (20 mg, 0.097 mmol), N1,N2-dimethylethane-1,2-diamine (5 mg, 0.049 mmol), copper iodide (4 mg, 0.020 mmol), and potassium phosphate (43 mg, 0.197 mmol) 2 mL of N-methylpyrrolidone was heated to 70 C. After allowing the reaction to stir overnight (17 h) at 70 C., the reaction was complete and allowed to cool to room temperature. The reaction was extracted 3X’s with EtOAc (3*5 mL) and 2X’s with NaHCO3 (3*10 mL). The crude organic layers were combined, dried over anhydrous Na2SO4 (s), filtered and then concentrated in vacuo. The crude mixture was then purified using the ISCO flash chromatography system using a 0-100% EtOAc/100-0% Hexane gradient mixture. A second column was done on the impure product using a gradient of MeOH/CHCl3 after which, the appropriate fractions were concentrated, to afford a yellow solid (17 mg, 52%). 1H NMR (DMSO) delta: 8.01 (s, 1H), 7.79 (d, J=6.0, 1H), 6.34 (d, J=6.0, 1H), 6.24 (m, 1H), 6.15 (d, J=7.0 Hz, 2H), 4.00 (br. S, 2H), 3.22 (s, 2H), 2.64 (t, j=5.3 Hz, 2H), 2.20 (s, 3H)

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; Allergan, Inc.; Wurster, Julie; Yee, Richard; Hull III, Clarence Eugene; Malone, Thomas C.; (39 pag.)US2016/96832; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, 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 25016-20-0, Product Details of 25016-20-0

1-methyl-1H-pyrazole-5-carboxylic acid (35 mg, 0.28 mmol, 1.1 equiv.), HATU (109 mg, 0.29 mmol,1.15equiv.), DIPEA (37mg, 0.29mmol, 1.15equiv.) is dissolved in an appropriate amount of DMF, stirred for 10 minutes and then added (4-fluoro-2-(Trifluoromethyl)phenyl)(5-aminoindolin-1-yl)methanone (81 mg, 0.25 mmol, 1.0 equiv.), stirring at room temperature for 8 hoursTime. The TLC monitors the reaction in real time. After the reaction, dilute with water, extract the appropriate amount of ethyl acetate three times, combine the organic phase, and then use water,The mixture was washed with saturated NaHCO3 solution and saturated NaCl solution, and the organic layer was dried over anhydrous NaSO?Purification afforded N-(1-(4-fluoro-2-(trifluoromethyl)benzoyl)indolin-5-yl)-1-methyl-1H-pyrazole-3-carboxamide(80 mg, yield: 74%).

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

Reference:
Patent; Fudan University; Wang Yonghui; Yu Fazhi; Li Wei; (38 pag.)CN109232358; (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. 863548-52-1, name is (1-Methyl-1H-pyrazol-5-yl)methanamine, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

Step a. To a mixture of tert-butyl 2-chloro-4-(3-(2-oxopyrrolidin-l-yl)phenyl)-5,7-dihydro-6H- pyrrolo[3,4-d]pyrimidine-6-carboxylate (prepared as in step a of Example 289, 0.450 g, 1.086 mmol) and l-methyl-lH-pyrazol-5-yl)methylamine (CAS Number 863548-52-1; 0.180 g, 1.629 mmol) in 1,4-dioxane (100 ml) was added K2C03 (0.450 g, 3.258 mmol) at rt. The reaction mixture was degassed for 10 min before addition of Pd2(dba)3 (0.099 g, 0.108 mmol) and Xanthphos (0.062 g, 0.108 mmol). The reaction mixture was heated at 90C for 16 h. The resulting mixture was cooled to rt, poured into water (20 ml) and extracted with EtOAc (3 x 30 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (3.2% MeOH in DCM) yielding tert-butyl 2-(((l-methyl-lH-pyrazol-5- yl)memyl)amino)-4-(3-(2-oxopyrrolidin-l-yl)phenyl)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6- carboxylate (0.250 g, 0.511 mmol). LCMS: Method A, 1.858 min, MS: ES+ 490.41.

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; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 35100-92-6,Some common heterocyclic compound, 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine, molecular formula is C5H9N3, 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 9 Preparation of N-(1,5-dimethylpyrazol-3-yl)-2,6 dimethyl benzamide (compound 3) To a cooled (0-5 C.) solution of 3-amino-1,5-dimethyl pyrazole (95%, 32.7 g, 0.28M) in anhydrous CH2 Cl2 (200 ml) was added a CH2 Cl2 (100 ml) solution of the 2,6 dimethyl benzoyl chloride (23.6 g, 0.14M). The reaction mixture was allowed to room temperature for 18 hours and then CH2 Cl2 was concentrated to give an oily mixture which was diluted in AcOEt. This suspension was then treated with saturated NaHCO3. After usual work-up, the crude material was cristallized with diisopropyloxide to give 13 g of the desired amide (38%: yield based on the 2,6-dimethyl benzoyl chloride). m.p.: 184 C.

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

Reference:
Patent; Novapharme; US5464860; (1995); 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. 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Formula: C8H10F2N2O2

ethyl 5-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate containing 0.2 area%, Purity 96.6 area% of ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate 10.0 g (0.05 mol), toluene 94 g, water 15.2 g, 25 wt% sodium hydroxide aqueous solution 1.8 g (0.07 mol) were added to the 200ml round-bottomed flask, while stirring it was heated in an oil bath and reacted under reflux for 23 hours. After cooling to room temperature, 15 mass% hydrochloric acid 21.0 g (0.09 mol) was dropped from the dropping funnel. After dropping, after cooling for 1 hour in an ice-water bath, using a 5C filter paper, suction filtered through a Kiriyama funnel, the filtrate was washed with 2 volumes of cold water. The obtained filtrate was dried under reduced pressure at 80 C. for 4 hours and got 8.60 g of crystals. When this crystal was analyzed by HPLC, it was 3- (difluoromethyl) -1-methyl -1H- pyrazole-4-carboxylic acid : 99.2 area %, 5- (difluoromethyl) -1-methyl-1 H-pyrazole-4-carboxylic acid : 0.1 area %. The toluene layer obtained by separating the filtrate into two layers, after concentrated in an evaporator, dried under reduced pressure at 80 C for 4 hours, got 0.02 g of crystals. When this crystal analyzed by HPLC, it was 3- (difluoromethyl) -1-methyl -1H- pyrazole-4-carboxylic acid : 27.2 area %, 5- (difluoromethyl) -1-methyl-1 H-pyrazole-4- carboxylic acid: 15.0 area %.

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; CENTRAL GLASS COMPANY LIMITED; IMURA, HIDEAKI; TAKADA, NAOTO; (11 pag.)JP5830957; (2015); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1192-21-8, 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. 1192-21-8 name is 1-Methyl-1H-pyrazol-5-amine, 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.

To the solution containing the amine compound (A-1), 700 mL of methanol was added. While stirring the obtained solution at an internal temperature of 5 ° C., To this solution, 120 g of an 85percent by mass aqueous solution of phosphoric acid (H 3 PO 4) (1.0 mol as H 3 PO 4) was added dropwise. By dropwise addition, Crystals precipitated. Precipitated crystals were collected by filtration, 111 g of crystals (slightly yellow to white crystals) of the organic amine salt (I-beta-2) were obtained (yield 57percent).

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

Reference:
Patent; FUJIFILM Corporation; Mikoshiba, Atsushi; (36 pag.)JP2017/19914; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 876343-24-7,Some common heterocyclic compound, 876343-24-7, name is 1-Ethyl-1H-pyrazol-4-amine, molecular formula is C5H9N3, 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.

[2]; 2-(6-Chlorobenzotriazol- 1 -yl)- 1 , 1 ,3,3-tetramethyluronium tetrafluoroborate was used in place of 2-(7-azabenzotriazol-l-yl)-l,l53,3-tetramethyluronium hexafluorophosphate(V) as the coupling agent. The product gave the following characterising data :- 1H NMR Spectrum: (DMSOd6) 1.32 (t, 3H), 3.61 (s, 2H), 3.77 (s, 3H), 4.07 (q, 2H), 6.76 (d, IH), 6.92 (m, IH), 7.06 (d, IH), 7.38 (d, IH), 7.42 (s, IH)5 7.88 (s, IH), 8.08 (s, IH), 8.92 (d, IH), 9.57 (s, IH), 10.05 (s, IH); Mass Spectrum: M+H+ 438 and 440.

The synthetic route of 876343-24-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics