Tag: M.W:100-200

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. 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

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

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

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

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

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 96799-02-9 as follows. Quality Control of 5-(Furan-2-yl)-1H-pyrazol-3-amine

EXAMPLE 50 6-Fluoro-3-[(5-furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-1,3-dihydro-indol-2-one The named compound is prepared by substituting E & Z-3-[(hydroxy)-methylene]-6-fluoro-1,3-dihydro-indol-2-one for E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one and 5-furan-2-yl-1H-pyrazol-3-ylamine for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-6-fluoro-1,3-dihydro-indol-2-one (0.033 gms.) is reacted with 0.061 gms. 5-furan-2-yl-1H-pyrazol-3-ylamine by refluxing in tetrahydrofuran (0.88 mL) to afford the named compound in the amount of 0.0263 gms.

According to the analysis of related databases, 96799-02-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan, Inc.; US6559173; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 10199-68-5, name is 4-Phenyl-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 10199-68-5, HPLC of Formula: C9H8N2

[0464] a mixture consisting of compound 21a (500 mg, 2.12 mmol), compound 21b (306 mg, 2.12 mmol) and Cs2CO3 (2.07 g, 6.36 mmol) was stirred at 110.6 C for 16 hrs. The reaction mixture was cooled to room- temperature, filtered and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography (petroleum ether: ethyl acetate = 3:2 and then acetic acid: ethyl acetate = 1: 100) to afford compound 21c (80 mg, 12.61% yield) as a light yellow solid, and compound 21d (125 mg, 21.73% yield) as a yellow solid.

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, 4-Phenyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

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

These common heterocyclic compound, 637336-53-9, name is Methyl 4-amino-1-methyl-1H-pyrazole-3-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. category: pyrazoles-derivatives

A solution of compound from step a (775 mg, 5 mmol), 1-chloro-2-(2-chloroethoxy)ethane (1420 mg, 10 mmol), KI (1660 mg, 10 mmol) and K2CO3 (2070 mg,15 mmol) in DMF (60 mL) was stirred for 3 hours at 120 oC. The solvent was removed and it was purified by reverse phase C18 column chromatography (MeCN/H2O) to give desired compound as a light yellow solid. (450 mg, 40%). ESI-MS m/z: 226.0 [M+H]+.

The synthetic route of Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; LIN, Kai; RHODIN, Michael, H.J.; McALLISTER, Nicole, V.; OR, Yat, Sun; (447 pag.)WO2019/67864; (2019); 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. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H6N2O2

To a solution of i-methyl-I H-pyrazole-5-carboxylic acid (5.28 g, 41.9 mmol) in dichloromethane (55 ml) was added oxalyl chloride (9.14 ml, 104.8 mmol) followed by 3 drops of dimethylformamide. The reaction was stirred at room temperature for 18 hours before concentration in vacuo. The residue was dissolved in acetonitrile (42 ml) and added dropwise to a cooled solution of 3- (2-chloro-5-methoxyphenyl)pyridine-2,6-diamine (preparation 1 , 9.5 g, 38 mmol) and lutidine (6.6 ml, 57.1 mmol) in acetonitrile (650 ml). The reaction was allowed to warm to room temperature and stirred under nitrogen for 2 hours. The reaction was quenched by the addition of water (300 ml) and concentrated to low volume in vacuo. The aqueous residue was washed with dichloromethane (2×300 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with ethylacetate: heptane 1 :4 to furnish a solid. This was recrystallised from toluene (100 ml) to afford 6.7 g of the title product. LCMS Rt=1.88 min MS m/z 358 [MH]+1HNMR (alphafe-DMSO): 3.75 (s, 3H), 4.05 (s, 3H), 5.3 (br s, 2H), 6.9 (m, 1 H), 6.95 (m, 1 H), 7.2 (m, 1 H), 7.3 (m, 1 H), 7.35 (m, 1 H), 7.45 (m, 1 H), 7.5 (m, 1 H), 10.3 (br s, 1 H).

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; PFIZER LIMITED; WO2008/135826; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics