Day: July 5, 2021

Some common heterocyclic compound, 35277-02-2, name is 4-Fluoro-1H-pyrazole, molecular formula is C3H3FN2, 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: C3H3FN2

To a mixture of 60% sodium hydride (56 mg) and THF (15 mL) was added 4-fluoro-1H-pyrazole (103 mg) at 0C. The mixture was stirred at 0C for 1 hr, and to the mixture was added 2,4-difluoro-1l-nitrobenzene (0.110 mL). The mixture was stirred overnight at room temperature, to the mixture was added saturated aqueous ammonium chloride solution at 0C, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (155 mg). MS: [M+H]+226.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35277-02-2, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; ITO, Masahiro; SUGIYAMA, Hideyuki; KUBO, Osamu; KIKUCHI, Fumiaki; YASUI, Takeshi; KAKEGAWA, Keiko; IKEDA, Zenichi; MIYAZAKI, Tohru; ARIKAWA, Yasuyoshi; OKAWA, Tomohiro; YONEMORI, Jinichi; TOITA, Akinori; KOJIMA, Takuto; ASANO, Yasutomi; SATO, Ayumu; MAEZAKI, Hironobu; SASAKI, Shinobu; KOKUBO, Hironori; HOMMA, Misaki; SASAKI, Minoru; IMAEDA, Yasuhiro; (500 pag.)WO2019/27054; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 34334-96-8, These common heterocyclic compound, 34334-96-8, name is 3-Methyl-5-nitro-1H-pyrazole, 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 7 Preparation of 2-(5-methyl-3-nitro-1H-pyrazol-1-yl)ethanol A solution of 5-methyl-3-nitro-1H-pyrazole (500 mg, 3.93 mmol) and potassium carbonate (1.08 g, 7.81 mmol) in acetonitrile (20 mL) was treated dropwise with 2-iodoethanol (2.00 g, 11.6 mmol) and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted with ethyl acetate (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, heptane to 1:1 ethyl acetate/heptane) to afford 2-(5-methyl-3-nitro-1H-pyrazol-1-yl)ethanol as a white solid: 1H NMR (400 MHz, DMSO-d6.) d 6.82 (s, 1H), 4.97 (t, J=5.2 Hz, 1H), 4.19 (t, J=5.2 Hz, 2H), 3.75 (q, J=5.2 Hz, 2H), 2.35 (s, 3H).

The synthetic route of 34334-96-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Connecticut, Inc.; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Mitchell, Scott A.; Schmitt, Aaron C.; Xu, Jianjun; Zhao, Zhongdong; US2014/148430; (2014); 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. 116008-52-7, name is 4-Amino-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C4H5N3O2

EXAMPLE 125 Trans-3-(naphth-2-yl)-but-2-enoic acid-N-(3-carboxy-1H-pyrazol-4-yl)-amide Prepared analogously to Example 31 from trans-3-(naphth-2-yl)-but-2-enoic acid chloride and 4-amino-1H-pyrazol-3-carboxylic acid in dimethylformamide with the addition of pyridine.

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; Boehringer Ingelheim Pharma KG; US6362210; (2002); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 151521-41-4, name is 4-Propyl-1H-pyrazol-3-amine, 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. Recommanded Product: 151521-41-4

(A) In the same manner as described in the step (B) of Reference Example 11, 4.5 g of N-(4-n-propyl-1H-pyrazol-3-yl)acetamidoxime was obtained from 7.2 g of 3-amino-4-n-propyl-1H-pyrazole and 9.3 g of triethyl orthoacetate.

The synthetic route of 4-Propyl-1H-pyrazol-3-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5475114; (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. 52867-42-2, name is Methyl 2-methyl-5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 2-methyl-5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate

c) 5-[3-Butyl-5-(l,2-dihydroxy-2-phenyl-ethyl)-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3- carboxylic acid methyl esterTo a stirred solution of 5-hydroxy-2H-pyrazole-3-carboxylic acid methyl ester (937 mg, 6.0 mmol) and [3-butyl-5-([E]-styryl)-isoxazol-4-yl]-methanol (1.54 g, 6.0 mmol) in THF (120 mL) at 5 0C under argon was added triphenylphosphine (2.1 g, 7.8 mmol), then diethyl azodicarboxylate (1.06 g, 6.0 mmol) was added dropwise. The reaction mixture was warmed to room temperature overnight. The reaction mixture was then poured into aqueous sodium chloride (saturated) and the mixture was extracted with ethyl acetate. The combined organic layers were then washed with water and saturated sodium hydrogen carbonate solution and then dried over sodium sulfate, filtered and evaporated. Concentration and purification by chromatography (silica, heptane:ethyl acetate = 4:1 to 7:3) afforded the intermediate product (1.07 g, 45%) as a yellow oil. MS: m/e = 396.2 [M+H]+. To a solution of the intermediate product (0.79 g, 2.0 mmol) in tert-butanol (50 mL) was added AD Mix-alpha (2.8 g) with water (50 mL). The reaction mixture was stirred at room temperature overnight and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated to a yellow oil. The crude material was purified by flash chromatography (silica gel, heptane:ethyl acetate 7:3 to 1 :1) to afford the title compound (440 mg, 51%) as a colorless oil. MS: m/e = 430.2 [M+H]+.

The synthetic route of 52867-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JAKOB-ROETNE, Roland; LUCAS, Matthew, C.; THOMAS, Andrew; WO2010/127975; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31108-57-3, 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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 4: 3,5-dibromo-lH-pyrazole-4-carbonitrile To lH-pyrazole-4-carbonitrile (6.76 g, 52.2 mmol) purchased from Aldrich (catalog number CDS008901) were added ethanol (150 mL) and water (225 mL). Then sodium acetate (29.1 g, 355 mmol) was added and the mixture was stirred until solids completely dissolved. Then bromine (10.75 mL, 209 mmol) was added dropwise. After 2 hours the reaction was complete. The reaction was diluted with water then extracted with DCM (3X150ml). The combined organic phases were washed with a saturated aqueous solution of sodilum thiosulfate (Na2S203). Poor layer seperation was observed in separating funnel, so water was added until DCM layer was in the bottom. The organic phase was then dired over MgS04, filtered and concentrated to form a solid. Purification: the solid was first dissolved in EtOAc. When the entire solid was dissolved, additional EtOAc was added to almost double the starting volume. Then hexane was added until solution turned slightly cloudy. After 30 min decantation, the small amount of precipitate formed in the flask was filtered, a dark brown oil left on the filter. The much lighter amber color solution that filtered though was then concentrated and contained mostly the desired product of 3,5-dibromo-lH-pyrazole-4-carbonitrile (8.9 g, 35.5 mmol, 68.0 % yield), it was used without further purification. No proton in the structure (only NH), no NMR spectrum. LCMS: the compound does not ionize.

The chemical industry reduces the impact on the environment during synthesis 1H-Pyrazole-4-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; NEW YORK UNIVERSITY SCHOOL OF MEDICINE; ALONSO PADILLA, Julio; CHARNLEY, Adam Kenneth; COTILLO TORREJON, Ignacio; ELBAN, Mark; HUGHES, Terry Vincent; KESSLER, Albane Marie; KNAPP-REED, Beth Anne; LIAN, Yiqian; MARTIN, Jose Julio; PENA URQUIZA, Imanol; RODRIGUEZ FERNANDEZ, Ana; (37 pag.)WO2016/55607; (2016); 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. 1369959-12-5, name is 3-Chloro-5-nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C3H2ClN3O2

Tin (II) chloride (12.8 g, 68 mmol) was added in portions to a solution of 3-chloro-5-nitro- lH-pyrazole (2.0 g, 13.6 mmol) in methanol (200 mL) and cone. HCl (10 mL) at 0 C. The reaction mixture was stirred at room temperature for 6 hours, and the organic solvent was removed under reduced pressure. The residue was diluted with water (20 mL), neutralized to pH 7 with Na2C03, then extracted with EtOAc (3 x 50 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (1.4 g, 87%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6): delta 11.55 (bs, 1H), 5.26 (s, 2H), 5.21 (s, 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; CORNELL UNIVERSITY; DANA-FARBER CANCER INSTITUTE, INC.; CHILDREN’S MEDICAL CENTER CORPORATION; MELNICK, Ari, M.; GABAS, Lorena, Fontan; US, Ilkay; CASALENA, Gabriella; GRAY, Nathanael, S.; SCOTT, David, A.; HATCHER, John; DU, Guangyan; WU, Hao; QIAO, Qi; (157 pag.)WO2018/85247; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 16034-46-1,Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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 100 mL round bottom flask was charged with a solution of 2-methylpyrazole-3- carboxylic acid (0.2662 g, 2.1107 mmol), EDC HCL (0.5634 g, 2.8782 mmol) and HOBt (0.389 g, 2.8782 mmol) in DMF (5 mL) and the reaction mixture stirred for 5 min at rt then N,N-diisopropylethylamine (0.7440 g, 5.7565 mmol) was added and the mixture stirred for 5 min. Then was added a solution of tert-butyl 5-[[3-(3-aminophenyl)-1,2,4-thiadiazol-5-yl]-tert- butoxycarbonyl-amino]-4-chloro-indazole-1-carboxylate (1.042 g, 1.9188 mmol) in DMF (5mL) and the solution stirred at room temperature for 24 h. Then, solvents were removed under vacuum and the resulting residue was purified by silica gel chromatography (40 g column, HP 15-40 uM 60 A flash cartridge from Silicycle) eluting with 0 to 50% hexanes/EtOAc to yield the title compound (0.717 g, 57.386% yield) as a light yellow foam.

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

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, D.; PADILLA, Fernando; SKALITZKY, Donald, J.; TOOGOOD, Peter, L.; VANHUIS, Chad, A.; (172 pag.)WO2018/39539; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1001020-13-8, name is (3-Trifluoromethyl-1H-pyrazol-4-yl)methanol, 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. Safety of (3-Trifluoromethyl-1H-pyrazol-4-yl)methanol

b) 3-(trifluoromethyl)-7H-pyrazole-4-carbaldehyde(3-(trifluoromethyl)-7/-/-pyrazol-4-yl)methanol (600 mg, 3.61 mmol) was dissolved in MeCN (5 ml_). MnO2 (785 mg, 9.03 mmol) was added. The reaction mixture was heated at 120 0C for 5 min in the microwave. The reaction mixture was filtered through decalite, washed with MeCN (30 ml_), then concentrated in vacuo and purified by flash column chromatography (silica gel; eluent EtOA?heptane, 1 :1) to give the desired product (200 mg, 1.22 mmol, 34 %). 1 H NMR (400MHz, CD3OD): delta 8.44 (s, 1 H), 9.95 (s, 1 H)

The synthetic route of (3-Trifluoromethyl-1H-pyrazol-4-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2008/3452; (2008); 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. 13808-62-3, name is 4-Methyl-3-phenyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H10N2

Part A — alpha,4-Dimethyl-3-phenylpyrazole-1-acetic acid Sodium hydride (50.0 g., 57% in oil, 1.2 mole) was added over 20 minutes to a stirred solution of 4-methyl-3-phenylpyrazole (158 g., 1.0 mole) in THF (1.0 l.) maintained at 10-20 C. Ethyl 2-bromopropionate (235 g., 1.3 mole) was added and the solution stirred for 18 hours, after which time ethanol was added and the solvent was removed by evaporation at reduced pressure. The residue was treated at 90 C. with sodium hydroxide (100 g., 2.5 mole) in 800 ml. 60% aqueous methanol for 30 minutes. After cooling, the solution was extracted with ether (3 * 200 ml.), and the aqueous phase was acidified with concentrated hydrochloric acid to give 148 g. of crude alpha,4-dimethyl-3-phenylpyrazole-1-acetic acid, m.p. 151-162 C. Recrystallization from aqueous methanol gave 111 g. of product, m.p. 168-172 C. The analytical sample was recrystallized from ethyl acetate, m.p. 170-172 C. Analysis: Calc’d for C13 H14 N2 O2: C, 67.81; H, 6.13; N, 12.17. Found: C, 68.32; H, 6.14; N, 12.06.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 13808-62-3.

Reference:
Patent; The Upjohn Company; US4072498; (1978); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics