Tag: M.W:100-200

Electric Literature of 20154-03-4, 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 20154-03-4 as follows.

To a stirred solution of 10 g (73.5 mmol) 3-(trifluoromethyl)-1H-pyrazole (3) in DMSO (150 ml) were added 9.9 g of potassium tert.-butoxide portion wise. After stirring for 5 minutes drop wise addition of 12 ml of iodoethane followed by stirring overnight were conducted. Water was added afterwards and the pH value was adjusted to 3 by using 1N HCl. The mixture was diluted with MTBE and extracted two more times with MTBE. The combined organic phase was washed with Na2S2O3-solution, water and brine yielding 8 g (67 percent) of the ionic liquid 8.

According to the analysis of related databases, 20154-03-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOLVAY SA; Braun, Max Josef; Fischer, Reiner; EP2662359; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31037-02-2, 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. 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

5-Amino-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (5.0 g, 29.6 mmol) was added portionwise to a mixture of tert-butyl nitrite (4.57 g, 44.3 mmol) and copper (II) bromide (7.92 g, 35.5 mmol) in acetonitrile (20 mL). The mixture was heated to 60C for 2 h. The resulting mixture was poured into 6M HCl (200 mL) and extracted with dichloromethane (3 x 250 mL). The combined organics was dried on magnesium sulfate and concentrated in vacuo. The crude material was purified by column chromatography (SiO2, 0% to 50% ethyl acetate in hexanes) to afford 5-bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester as an off-white solid (4.7 g, 68%). 1H NMR (CDCl3) : 7.93 (s, 1H), 4.32 (q, J = 7.2 Hz, 2H), 3.92 (s, 3H), 1.36 (t, J = 7.0 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BOLIN, David Robert; DE VICENTE FIDALGO, Javier; HERMANN, Johannes Cornelius; TIVITMAHAISOON, Parcharee; YI, Lin; ZAK, Mark; WO2013/189904; (2013); 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. 948570-75-0, name is 1-(2-Methoxyethyl)-4-nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H9N3O3

To a solution of l-(2-methoxyethyl)-4- nitro-pyrazole (3.0 g, 17.53 mmol) in MeOH (50 ml) was added 10 % Pd/C (300 mg) under N2. The suspension was degassed and purged with H2 several times. The mixture was stirred under a H2 atmosphere at 25 C for 3 h. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure to give the title compound as a red oil (Y = 97 %). NMR (400 MHz, chloroform-rf) d ppm 7.16 (s, 1H), 7.09 (s, 1H), 4.16 (t, J= 5 Hz, 2H), 3.69 (t, J= 5 Hz, 2H), 3.32 (s, 3H), 2.93 – 2.83 (hr. s, 2H).

According to the analysis of related databases, 948570-75-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NODTHERA LIMITED; HARRISON, David; WATT, Alan Paul; BOCK, Mark G.; (334 pag.)WO2019/121691; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 118430-74-3, 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. 118430-74-3 name is 3-Cyclopropyl-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.

Intermediate I12.2, (0.20 g), 3-cyclopropyl-1-methyl-1H-pyrazole-5-amine (0.14 g), potassium t-butoxide (0.10 ml of a 1M THF solution) and dioxane (2 ml) were transferred to a microwave vial and heated under microwave irradiation under the following conditions: max power 150 W, T 150 C., 15 min; after the first cycle 0.05 mL of base were added and two more cycles of irradiation performed under the same conditions. The reaction mixture was evaporated to dryness, and the oily residue was purified by preparative LC-MS affording example 208 (as TFA salt) (0.09 g). HPLC (Rt)=7.12 min (method P)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/261687; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 175137-46-9,Some common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, 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.

2,4-dichloropyrimidine 2 (13.30 g, 89.31 mmol) and 3-amino-5-cyclopropylpyrazole 1 (11.00 g, 89.31 mmol) were dissolved in tetrahydrofuran (TFA) (100 ml) followed by theaddition of deionized water (100 ml). The solution was then treated with potassium acetate (261.9 g, 2.5 mol). The resulting mixture was kept at 55C for 48 h. The mixture was filtered to remove excess potassium acetate. The organic layer was separated and dried using magnesium sulfate and concentrated before loading on an AnaLogix silica column. Intermediate 3 was separated as previously reported (34). ?H NMR (400 MHz, DMSO) oe 12.14 (s, 1H), 10.23 (s,1H), 1.84 (m, 1H), 0.88 (m, 2H), 0.64 (m, 2H). ?3C NMR (100 MHz, DMSO) oe 161.4, 160.7,160.0, 153.9, 148.6, 147.8, 146.8, 8.4, 8.2. MS calculated for C,0H,0N5 235.06, found 236.15 (M).

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SHOKAT, Kevan, M.; MENDEZ, Aaron, S.; (131 pag.)WO2016/22839; (2016); 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

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

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

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

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