Day: May 17, 2021

Reference of 143426-49-7, A common heterocyclic compound, 143426-49-7, name is (4-Pyrazol-1-yl-phenyl)methanol, molecular formula is C10H10N2O, 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.

To a stirred solution of 4-(1 H-pyrazol-1 -yl)phenyl)methanol (0.2 g, 1.14 mmol) in DCM (10 mL), SOCI2 (0.2 mL, 2.29 mmol) was added at 0 C and the reaction mixture was stirred for 2 h. After completion of reaction, the reaction mixture was concentrated under vacuum and co-distilled with DCM to get the title compound. It was used in the next step without further purification. Yield: (0.170 g, brown gummy solid). LCMS: (Method A) 193.1 (M+H), Rt. 3.46 min, 94.32% (Max).

The synthetic route of 143426-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; WISHART, Grant; KULKARNI, Santosh S.; RAKESH, Paul; (338 pag.)WO2020/39027; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 199678-06-3, name is 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid, molecular formula is C11H10N2O2, 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. Application In Synthesis of 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid

EXAMPLE 55 [4-(1-Methyl-1H-pyrazol-4-yl)-phenyl]-(5H,11H-pyrrolo[2,1-c][1,4]-benzodiazepin-10-yl)-methanone Oxalyl chloride (0.30 g) was added to a suspension of 4-(1-methyl-1H-pyrazol-4-yl)-benzoic acid (0.46 g) in dichloromethane (25 ml). Two drops of dimethylformamide were added and the mixture was stirred for 18 hours at room temperature. The resultant solution was evaporated to dryness to yield the crude acid chloride (0.57 g), which was utilized without further purification. The acid chloride was added to a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]-benzodiazepine (0.37 g) and diisopropylethylamine (0.58 g) in dichloromethane (50 ml). After 18 hours at room temperature, the reaction mixture was washed with water and saturated aqueous sodium bicarbonate. The dichloromethane solution was dried over anhydrous sodium sulfate and filtered through a short column of hydrous sodium magnesium silicate and further eluted with several volumes of dichloromethane. The combined organic phase was concentrated on a hot plate with the gradual addition of hexane until crystallization occurred. After cooling, the crystals were collected by filtration to yield the title compound (0.38 g), m.p. 200-201 C.; MS m/z: 368 (M)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 199678-06-3, its application will become more common.

Reference:
Patent; Wyeth; US6511974; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 199678-06-3, 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. 199678-06-3, name is 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Oxalyl chloride (0.30 g) was added to a suspension of 4-(1-methyl-1H-pyrazol-4-yl)-benzoic acid (0.46 g) in dichloromethane (25 ml). Two drops of dimethylformamide were added and the mixture was stirred for 18 hours at room temperature. The resultant solution was evaporated to dryness to yield the crude acid chloride (0.57 g), which was utilized without further purification.

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-(1-Methyl-1H-pyrazol-4-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; American Cyanamid Company; US6831079; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 873191-23-2, 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 873191-23-2 as follows.

General procedure: The phenanthridine skeletons1-8 (0.1 mmol) were dissolved in dryTHF (10 mL), and NaH (50 mg, 2 mmol), and 3-(bromomethyl)pyridine,3-(chloromethyl)-1,5-dimethyl-1H-pyrazole or 5-bromomethyl-1,3-dimethyl-1H-pyrazole (1 mmol) were added. The mixture was stirred atrt. for 12 h and quenched with H2O (50 mL) in an ice bath. The solutionwas evaporated to remove the THF and extracted with CH2Cl2(2×30 mL). The organic layer was washed with saturated NaHCO3 andbrine, dried over MgSO4, filtered and concentrated. The residue waspurified by column chromatography using petroleum-EtOAc as theeluent to afford about 35 mg of each phenanthridine compound.

According to the analysis of related databases, 873191-23-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Duo-zhi; Yang, Bi-juan; He, Xiao-li; Fan, Shi-rui; Cai, Jie-yun; Jing, Chen-xu; Zhang, Heng; Zhang, Yu; Li, Lin; Hao, Xiao-jiang; Bioorganic Chemistry; vol. 84; (2019); p. 285 – 294;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 10250-59-6, name is Methyl 1,3-dimethyl-1H-pyrazole-5-carboxylate, molecular formula is C7H10N2O2, 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. HPLC of Formula: C7H10N2O2

Example 1 : Preparation of N-(2,5-dimethyl-2H-pyrazol-3-ylmethyl)-4-(5-trifluormethyl- pyridin-2-yloxy)-benzenesulfonamide (Table I: example 1-21 )Example 1.1 : Preparation of (2,5-dimethyl-2H-pyrazol-3-yl)-methanol At 25 to 300C 25 ml of a 1 molar solution of lithium aluminium hydride in diethylether was added dropwise to 4.5 g 2,5-dimethyl-2H-pyrazole-3-caboxylic acid methyl ester in 50 ml diethylether. A solid precipitated and the reaction mixture was stirred for about 2 to 3 days at about 20 to 25C. After dilution of the reaction mixture with 50 ml of MTBE a little volume of water was added. After filtration the precipitated wet solid was thoroughly washed with ethyl acetate. The solvent was removed in vacuo from the combined filtrate and washing fluids to yield 3.7 g of the title compound. 1H-NMR (CDCI3, delta in ppm): 5.9 (s, 1 H); 4.6 (s, 2H); 4.0 (s, broad, 1 H); 3.75 (s, 3H); 2.2 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10250-59-6, its application will become more common.

Reference:
Patent; BASF SE; WO2009/101082; (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. 1072-91-9, name is 1,3,5-Trimethylpyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 1,3,5-Trimethylpyrazole

1,3, 5-Trimethyl-lH-pyrazole (630 mg, 5.71 mmol) cooled to [0 oC] was treated with oxalyl chloride (7.0 mL). The reaction was then warmed to [25 oC] and then heated to reflux for 4 h. At this time, the reaction was cooled to [25 oC] and was stirred at [25 oC] for 24 h. At this time, the excess oxalyl chloride was removed by distillation. The resulting residue was cooled to [0 oC] and treated with ice/water (15 mL). The mixture was slowly warmed to [25 oC] over 4 h. At this time, the resulting solids were collected by filtration, washed with water, and dried in vacuo to afford [OXO- (1,] 3,5- [TRIMETHYL-LH-PYRAZOL-4-YL)-ACETIC] acid (700 mg, 70%) as brown solid

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; F. HOFFMANN-LA ROCHE AG; WO2003/106459; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 89260-46-8,Some common heterocyclic compound, 89260-46-8, name is 3-(1H-Pyrazol-3-yl)aniline, molecular formula is C9H9N3, 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.

(2S)-N-(3-(lH-pyrazol-3-yl)phenyl)-2-amino-3-phenylpropanamide (12.C).To a solution of 3-(lH-pyrazol-3-yl)benzenamine 12.B (400 mg, 2.52 mmol) in DMF (5 mL) was added (S)-2-(tert-butoxycarbonyl)-3-phenylpropanoic acid (795 mg, 3.02 mmol, available from Aldrich), diisopropylethylamine (0.65 mL, 3.75 mmol) and 2-(1H- Benzotriazole-l-yl)-l,l,3,3-Tetramethyluronium hexafluorophosphate (1.14g, 3.02 mmol). The resulting mixture was stirred overnight at room temperature. The mixture was then partitioned between water (50 mL) and EtOAc (50 mL). The layers were separated and the aqueous phase was extracted with additional EtOAc (2 x 5OmL). The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated. [0253] The crude intermediate was then stirred in HCl solution (4M in dioxane, 5 mL) for Ih. The mixture was then concentrated, the resulting white solid was neutralized with NaHCO3 saturated solution (5 mL) and extracted with DCM (2 x 5mL) to afford (2S)-N-(3- (lH-pyrazol-3-yl)phenyl)-2-amino-3-phenylpropanamide 12.C as a colorless film (200mg, 26% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(1H-Pyrazol-3-yl)aniline, its application will become more common.

Reference:
Patent; AMGEN INC.; DU, Xiaohui; FU, Zice; HOUZE, Jonathan, B.; JIAO, Xianyun; KIM, Yong-jae; LI, Leping; LIU, Jinqian; LIZARZABURU, Mike; MEDINA, Julio; SHEN, Wang; TURCOTTE, Simon; YU, Ming; WO2010/93849; (2010); A2;,
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. 25700-12-3, name is 3-(1H-Pyrazol-1-yl)pyridine, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

Under argon, 3-(4-bromopyrazol-1-yl)pyridine (1.00 g, 4.46 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (dppf) (74 mg, 0.13 mmol), palladium dichloride-dppf (109 mg, 0.13 mmol), potassium acetate (1.31 g, 13.3 mmol) and pinacolatodiborane (1.19 g, 4.68 mmol) were added to dioxane (11 ml). The mixture was heated under reflux for 24 h and then cooled. The solvent was removed on a rotary evaporator under reduced pressure, dichloromethane (100 ml) and water (100 ml) were added to the residue, and the solids formed were filtered off with suction and discarded. The filtrate was extracted with dichloromethane and the organic phase was dried over magnesium sulphate. The solvent was removed on a rotary evaporator under reduced pressure and the residue was chromatographed (ethyl acetate, cyclohexane).Yield: 680 mg (55% of theory), logP(HCOOH) 2.19, [M++1] 272.21H NMR (d6-DMSO): 1.30 (s, 12H), 7.51 (m, 1H), 7.90 (s, 1H), 8.25 (m, 1H), 8.51 (m, 1H), 8.73 (s, 1H), 9.12 (m, 1H).

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; BAYER CROPSCIENCE AG; US2012/165345; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1001020-17-2,Some common heterocyclic compound, 1001020-17-2, name is 3-(tert-Butyl)-1H-pyrazole-4-carbaldehyde, molecular formula is C8H12N2O, 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 78 2-(2-(3-7erf-butyl-4-formyl-1H-pyrazol-1-vnacetan?ido)-N-nnethyl-4,5.6,7- tetrahvdrobenzofblthiophene-3-carboxannide3-Terf-butyl-1H-pyrazole-4-carbaldehyde (150 mg, 0.986 mmol), 2-(2-bromoacetamido)- N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxannide (490 mg, 1.478 mmol) and potassium carbonate (545 mg, 3.94 mmol) were mixed with DMF (5 ml_) and heated for 3 h at 60 0C. The reaction was partitioned between water and EtOAc. Organics were combined and purified by chromatography (0-60%, EtOAc/heptane) to give the title product as a white solid (360 mg, 0.894 mmol, 91 %). MS (ESI): m/z 403.6 [M + H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(tert-Butyl)-1H-pyrazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; N.V. ORGANON; WO2008/3452; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1239726-11-4,Some common heterocyclic compound, 1239726-11-4, name is 1-(2-Fluorophenyl)-5-methoxy-1H-pyrazole-3-carboxylic acid, molecular formula is C11H9FN2O3, 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.

Synthesis example 9Ethyl (S)-3-{[1 -(2-fluoro-phenyl)-5-methoxy-1 H-pyrazole-3-carbonyl]-amino}-3-(2- methyl-phenyl)-propionate Step 1 : 1 -(2-Fluoro-phenyl)-5-methoxy-1 H-pyrazole-3-carbonyl chlorideA suspension of 1 -(2-fluoro-phenyl)-5-methoxy-1 H-pyrazole-3-carboxylic acid (39.1 g, 167 mmol) in 2-methyltetrahydrofuran (300 ml) was cooled to 0 C and DMF (293 muIota, 3.81 mmol) was added. Oxalyl chloride (23.1 g, 182 mmol) was added dropwise. After 16 h at room temperature ca. 100 ml of the solvent were removed by distillation. The resulting suspension of the title compound was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Fluorophenyl)-5-methoxy-1H-pyrazole-3-carboxylic acid, its application will become more common.

Reference:
Patent; SANOFI; RUF, Sven; PERNERSTORFER, Josef; SADOWSKI, Thorsten; HORSTICK, Georg; SCHREUDER, Herman; BUNING, Christian; OLPP, Thomas; SCHEIPER, Bodo; WIRTH, Klaus; WO2011/92187; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics