Tag: M.W:100-200

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 42027-81-6 as follows. HPLC of Formula: C5H7N3O3

A 100 mL round-bottom flask was charged with a solution of intermediate 28.2 (500 mg, 3.18 mmol, 1.00 equiv) in methanol (20 mL) and palladium on carbon (100 mg). To the above hydrogen gas was introduced. The resulting solution was stirred for 2 h at room temperature. The solids were filtered out and mixture was concentrated under vacuum to provide 350 mg (crude) of intermediate 28.3 as yellow oil. LCMS (ES, m/z): 128 [M+H].

According to the analysis of related databases, 42027-81-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 133261-11-7, These common heterocyclic compound, 133261-11-7, name is Ethyl 3-cyclopropyl-1-methyl-1H-pyrazole-5-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.

General procedure: 2a (0.05 mol) was added to a stirred mixture of NaOH (6.0 g, 0.15 mol) and water (100 mL). After 4 h under 80 C, the mixture was poured into ice water and the pH was adjusted to acidic. Then 10 % HCl was slowly added to the solutions until a large amount of solids precipitated. After filtration, the solids were dried; 4.6 g (92 % purity) white solid (3a) was obtained. Yield 60 %; GC-MS (EI, 70Ev) (m/z 140 (M+). 3b-p were synthesized in a similar procedure.

Statistics shows that Ethyl 3-cyclopropyl-1-methyl-1H-pyrazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 133261-11-7.

Reference:
Article; Huang, Danling; Huang, Mingzhi; Liu, Weidong; Liu, Aiping; Liu, Xingping; Chen, Xiaoyang; Pei, Hui; Sun, Jiong; Yin, Dulin; Wang, Xiaoguang; Chemical Papers; vol. 71; 11; (2017); p. 2053 – 2061;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 5334-39-4, 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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of PPh3 (4.28 g, 0.016 mole, 1.1 equiv) and DIAD (3.33 gm,, 0.016 mole, 1.1 equiv) in THF (2mL), was added 4-nitro-lH-pyrazole (1.96 g, 0.004 mmol, 1.0 equiv) The reaction mixture was added l-[2, 4-bis (trifluoromethyl) phenyl] ethanol (4 g, 0.004 mmol, 1.0 equiv). The reaction mixture was stirred at room temperature for 1 hrs. Product formation was confirmed with TLC and LCMS. After completion of reaction mixture were diluted with EtOAc (50 mL) and washed with water (3×50 mL). Organic layer dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain crude which was further purified by flash column chromatography to obtain pure product l-(l-(2,4- bis(trifluoromethyl)phenyl)ethyl)-5-methyl-4-nitro-lH-pyrazole (0.5 gm) and l-(l-(2,4- bis(trifluoromethyl)phenyl)ethyl)-3-methyl-4-nitro-lH-pyrazole (1.5 gm). LCMS: 368 [M+H] +.

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

Reference:
Patent; PRAXIS BIOTECH LLC; ALFARO, Jennifer; BELMAR, Sebastian; NUNEZ VASQUEZ, Gonzalo Esteban; PUJALA, Brahmam; SATHE, Balaji Dashrath; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; THAKRAL, Pooja; PATIDAR, Rajesh Kumar; (344 pag.)WO2019/195810; (2019); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C5H6N2O, 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

Preparation 65: 3 ‘-Chloro-4-( 1 -methyl- 1 H-pyrazol-4-ylmethyl)-3 ,4,5 ,6-tetrahydro-2H- [l,2′]bipyrazineDissolve 3′-chloro-3,4,5,6-tetrahydro-2H-[l,2’]bipyrazinyl (3.43 g, 17.3 mmol) in tetrahydrofuran (100 mL). Add 1 -methyl- lH-pyrazole-4-carbaldehyde (2.244 g, 20.38 mmol) in dry tetrahydrofuran (5 mL), stir for 10 min. at room temperature, add sodium triacetoxyborohydride (4.32 g, 20.4 mmol) and subject the reaction to ultrasound stirring for 6 hr. at room temperature. Add saturated aqueous sodium hydrogen carbonate (100 mL) then 2 N sodium hydroxide (10 mL) to the mixture and extract with DCM (2 x 200 mL). Pass the combined DCM extracts through an 1ST Phase Separator Frit, concentrate and purify (silica gel chromatography, eluting with 0: 100 to 8:92 methanol:DCM), to give the title preparation as a crystalline solid (5.21 g, 92%). MS (ES): m/z = 293.1 [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 25016-11-9, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/141020; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 42098-25-9, These common heterocyclic compound, 42098-25-9, name is 5-Chloro-1-methyl-4-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.

tert-Butyl 8-(1-methyl-4-nitro-1H-pyrazol-5-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate A mixture of 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 (150 mg, 0.93 mmol), tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (244 mg, 1.02 mmol) and DIPEA (1 mL) in EtOH (3 mL) was heated at 130 C. in a microwave for 2 hr. The solvent was removed under reduced pressure and the crude product was purified via silica gel column chromatography (50% EtOAc/isohexane) to give tert-butyl 8-(1-methyl-4-nitro-1H-pyrazol-5-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate as a yellow oil (245 mg, 72%). 1H NMR (400 MHz, CDCl3) delta 8.02 (s, 1H), 3.76 (s, 3H), 3.49-3.39 (m, 2H), 3.30-3.00 (m, 6H), 1.90-1.60 (m, 6H), 1.55 (s, 9H).

Statistics shows that 5-Chloro-1-methyl-4-nitro-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 42098-25-9.

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 55864-87-4, These common heterocyclic compound, 55864-87-4, name is Ethyl 4-nitro-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.

A mixture of 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester (6.40 g, 34.6 mmol) and 10% Pd/C (650 mg) in EtOH (150ml) was stirred under an atmosphere of hydrogen for 20 h. The mixture was filtered through a plug of Celite, reduced in vacuo and dried through azeotrope with toluene to afford 4-amino-1H-pyrazole-3- carboxylic acid ethyl ester as a pink solid (5.28 g, 98%). (1H NMR (400 MHz1 DMSO-d6) D 12.7 (s, 1 H), 7.1 (s, 1 H), 4.8 (s, 2H), 4.3 (q, 2H), 1.3 (t, 3H)).

The synthetic route of 55864-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77424; (2006); A1;; ; Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77425; (2006); 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. 15802-80-9, name is 3-(tert-Butyl)pyrazole, A new synthetic method of this compound is introduced below., Product Details of 15802-80-9

Sodium hydride (60% suspension in oil, 0.12 g, 3.0 mmol) was washed with hexane, dried under nitrogen and resuspended in dry dimethylformamide (10 mL). 3-tert-butylpyrazole (0.20 g, 1.6 mmol) was added in one portion at ambient temperature, and the stirring was continued until the gas evolution subsided. The (5,11-dihydro-pyrido [2,3-b] [1,5] benzodiazepin-6-yl)- [4-fluoro-2-trifluoromethylphenyl]-methanone of Example 4, Step B (0.50 g, 1.3 mmol) was added in one portion to the clear solution. The mixture was placed in an oil bath (preheated at 130C) for 30 minutes and then heated at reflux for 5 hours. After cooling, the mixture was partitioned between water and ethyl acetate. The organic extracts were dried over sodium sulfate and evaporated to dryness. The crude residue was dissolved in dichloromethane and absorbed onto a silica Merck-60 flash column. Elution with 25% ethyl acetate in hexane provided the title product (0.23 g, 36.0%) as a foam which crystallized by trituration with hexane-ether, m.p. 136-140C. NMR (DMSO-d6, 400 MHz): delta 1.26 (s, 9H, C(CH3)3), 4.17 and 5.45 (dd, 2H, CONCH2), 6.47 (m, 1H, pyrazole CH), 6.54 (m, 1H), 6.68 (m, 1H), 6.80 (m, 1H), 7.00 (m, 1H), 7.28 (m, 1H), 7.60 (m, 1H), 7.87 (m, 1H), 8.04 (m, 1H), 8.13 (m, 1H), 8.47 (m, 1H, pyrazole CH), 9.62 (s, 1H, NH) MS (EI, m/z): 491 [M]+ Anal. Calc’d for C27H24F3N5O: C 65.98, H 4.92, N 14.25. Found: C 65.75, H 4.92, N 13.95

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; Wyeth; EP1000059; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, 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. Product Details of 632365-54-9

5-Amino-3-pyrazolcarboxylic acid methyl ester (16.91 g, 119.8 mmol) is dissolved in ethanol (2.4 L) and hydrochloric acid (37%, 12.5 mL, 150 mmol) is added. Then, a solution of 2-bromo-malonealdehyde (18.9 g, 125.2 mmol) is dissolved in ethanol (1.4 L) and is quickly added in a drop wise manner at RT. After 30 min, a precipitation is observed; after 6 hours the precipitate is removed and washed with 50 ml ethanol and thereafter with 50 ml diethyl ether. Here, 4.19 g of the clean product are isolated. After evaporation of the filtrate and crystallisation, additional 1.43 g product are obtained to yield 6-Bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid methyl ester (5.62 g, 18.3% d. Th.). In case of a smaller scale reaction with only 1 g of the starting amine 5-amino-3-pyrazolcarboxylic acid methyl ester, the yield is much better e.g. 68%.

The synthetic route of 632365-54-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; US2008/32998; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 103626-03-5, 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. 103626-03-5, name is Ethyl 1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A round bottom flask was charged with starting ethyl 3-hydroxy-1-methyl-4-pyrazolecarboxylate (100 mg, 0.588 mmol). The flask was placed under high vacuum for 5 min, then backfilled with nitrogen atmosphere. DMF (3 mL) was added, followed by sodium hydride (60% dispersion in mineral oil, 27 mg, 1.2 equiv.) at 20 C. The flask was stirred at 20 C. for 60 min, then 4-(2-iodoethyl)morpholine (184 mg, 1.3 equiv.) was added. The reaction was stirred at 80 C. for 16 hr. The reaction was removed from heating and allowed to cool to 20 C., then the reaction was quenched with water and extracted five times into ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to provide 120 mg crude product. Silica gel TLC (95:5 dichloromethane:methanol) of the crude product indicated complete consumption of starting aminopyrazole (Rf ?0.60) and one new UV-active product (Rf 0.50). The resulting residue was dissolved in dichloromethane and purified by flash column chromatography (silica gel, 12 g, 0 to 10% methanol in dichloromethane). The major UV-active product eluted at 5% dichloromethane. Fractions were assayed by silica gel TLC. The fractions containing the major UV-active product were collected and concentrated in vacuo to give ethyl 1-methyl-3-(2-morpholinoethoxy)-1H-pyrazole-4-carboxylate (120 mg). 1H NMR (400 MHz, Chloroform-d) delta 7.63 (s, 1H), 4.37 (t, J=5.7 Hz, 2H), 4.21 (q, J=7.1 Hz, 2H), 3.71 (s, 3H), 3.72-3.69 (m, 4H), 2.82 (t, J=5.7 Hz, 2H), 2.61 (t, J=4.7 Hz, 4H), 1.28 (t, J=7.1 Hz, 3H). LCMS-ESI+ (m/z): [M+H]+ calculated for C13H21N3O4: 284.2; found: 284.1.

The chemical industry reduces the impact on the environment during synthesis Ethyl 1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Gilead Sciences, Inc.; Chu, Hang; Guerrero, Juan A.; Hurtley, Anna E.; Hwang, Tae H.; Jiang, Lan; Kato, Darryl; Kobayashi, Tetsuya; Knox, John E.; Lazerwith, Scott E.; Li, Xiaofen; Lin, David W.; Medley, Jonathan W.; Mitchell, Michael L.; Naduthambi, Devan; Newby, Zachary; Squires, Neil H.; Tsui, Vickie H.; Venkataramani, Chandrasekar; Watkins, William J.; Yang, Hong; (292 pag.)US2019/352271; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 75415-03-1, These common heterocyclic compound, 75415-03-1, name is 2-(1H-Pyrazol-3-yl)pyridine, 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.

Under an argon atmosphere, copper hexahydrate perchlorate [Cu [C104] 2 · 6H20] (167 mg,0.45 mmol) and excess copper powder (230 mg, 3.62 mmol) were stirred in 8 mL of acetonitrile for 20 minutes,After which a solution of 1,4-bis [diphenylphosphine] butane (384 mg, 0.90 mmol) in 12 mL of dichloromethane was added,After stirring for 1 hour, a solution of 3- [2-pyridyl] pyrazole ligand (131 mg, 0.90 mmol) was added,The reaction was continued for 3 hours at room temperature. After filtration, the solvent was evaporated to dryness on a rotary evaporator,And recrystallized from a mixed solvent of dichloromethane (2 mL) and diethyl ether (20 mL) at a volume ratio of 1:10.Filtered and recrystallized to give colorless crystalline product which was washed 3-4 times with 25 mL of diethyl ether,After drying in vacuo, a white solid product was obtained as perchlorate ? bis [3- [2-Pyridyl] pyrazole] bis [mu-Mu-bis [diphenylphosphine] butane] bis [copper (II) complex] (456 mg, 0.31 mmol)was 69%.

The synthetic route of 75415-03-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi University of Science and Technology; Chen, Jinglin; Guo, Zonghao; He, lihua; Liu, Suijun; Wen, Herui; (13 pag.)CN104877673; (2016); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics