Day: June 24, 2021

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. 89088-55-1, name is 5-Bromo-1-methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H6BrN3

To a solution of 5-bromo-i-methyl-1H-pyrazol-3-amine (129 mg, 734.7 umol), 2- [3-(trifluoromethyl)phenyl]acetic acid (150 mg, 734.7 umo) in pyridine (2.0 mL) added EDCI (211 mg, 1.1 mmol). The mixture was stirred at 45C for 12 h. The reaction mixture was quenched by addition H20 (5.0 mL), extracted with dichloromethane 15.0 mL (5.0 mL x 3). The combined organic layers were washed with brine 15.0 mL (5 mL x 3), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (Si02, Petroleum ether / Ethyl acetate = i/i) to afford N-(5-bromo-i-methyl-1H- pyrazol-3 -yl)-2-(3 -(trifluoromethyl)phenyl)acetamide (150 mg, crude).

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; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (143 pag.)WO2018/222917; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. Quality Control of 4-Fluoro-1H-pyrazole

(5)-N-(2-Chloropyridin-4-yl)-3-(4-fluoro- lH-pyrazol- l-yl)-2-hydroxy-2-methylpropanam (0881) (0882) 1041 (0883) [00407] To a dry, nitrogen-purged 100 mL round-bottom flask equipped with a dropping funnel under argon atmosphere, NaH of 60% dispersion in mineral oil (96 mg, 2.4 mmol) was added in 10 mL of anhydrous THF solvent at ice-water bath. 4-Fluoro-lH-pyrazole (103 mg, 1.2 mmol) was added and the solution stirred 30 min at the ice-water bath. Into the flask, the solution of ( ?)-3-bromo- N-(2-chloropyridin-4-yl)-2-hydroxy-2-methylpropanamide (293 mg, 1.0 mmol) in 5 mL of anhydrous THF was added through dropping funnel under argon atmosphere at the ice- water bath and stirred overnight at RT. After adding 1 mL of H2O, the reaction mixture was condensed under reduced pressure, and then dispersed into 50 mL of EtOAc, washed with 50 mL (x 2) water, evaporated, dried over anhydrous MgS04, and evaporated to dryness. The mixture was purified with flash column chromatography using as an eluent EtOAc/hexane as a 1:2 ratio to produce compounds to produce the titled compound (55%) as a white solid. (0884) [00408] Compound 1041 was characterized as follows: lH NMR (400 MHz, CDCI3) delta 8.90 (bs, 1H, NH), 8.26 (d, = 5.6 Hz, 1H), 7.63 (s, 1H), 7.75 (d, = 4.2 Hz, 1H), 7.33 (d, = 4.2 Hz, 1H), 7.31 (dd, = 5.6, 1.2 Hz, 1H), 5.88 (s, 1H, OH), 4.53 (d, = 13.6 Hz, 1H), 4.14 (d, = 13.6 Hz, 1H), 1.45 (s, 3H); 19F NMR (CDCI3, decoupled) delta -176.47; MS (ESI) m/z 298.98 [M + H] +; 296.96 [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 35277-02-2, its application will become more common.

Reference:
Patent; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (234 pag.)WO2017/214634; (2017); 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. 400877-57-8, name is Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate

To a solution of methyl 1-methyl-4-nitro-pyrazole-3-carboxylate (2 g, 10.8 mmol, CAS400877-57-8) in MeOH (20 mL) was added Pd/C (200 mg, 10% wt) under N2 atmosphere. The suspension was degassed and purged with H2 gas 3 times. The mixture was stirred under H2 (15 Psi) at rt for 12 hr. On completion, the reaction mixture was filtered and concentrated in vacuo to give the title compound (1.68 g, 100% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta 6.95 (s, 1H), 3.92 (s, 3H), 3.86 (s, 3H).

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 400877-57-8.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
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 5071-61-4 as follows. SDS of cas: 5071-61-4

A solution of acid 4 (0.09 g, 0.47 mmol) in dry DMF (2 mL) treated sequentially with amine (5a-i, 6a-e and 7a-h; 0.517 mmol)and triethylamine (0.94 mmol) was stirred under a N2 atmosphere for 15 min, later TBTU (0.56 mmol) was added and reaction mixture refluxed for 4-10 h. The reaction mixture was quenched with aq satd NH4Cl solution (10 mL). After 10 min, it was diluted withCHCl3 (2 10 mL) and washed with water (10 mL), NaHCO3 solution(10 mL) and brine (10 mL). The organic layers were dried over anhydrous sodium sulfate, evaporated and the residue purified by column chromatography using 30% ethyl acetate in pet. ether to afford corresponding amides 8a-i, 9a-e and 10a-h.

According to the analysis of related databases, 5071-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Doma, Anuradha; Kulkarni, Ravindra; Palakodety, Radhakrishna; Sastry, G. Narahari; Sridhara, Janardhan; Garlapati, Achaiah; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 6209 – 6219;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5744-40-1, The chemical industry reduces the impact on the environment during synthesis 5744-40-1, name is Ethyl 1,3-dimethyl-1H-pyrazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

d. Alternative synthesis of 1.S-dimethylpyrazole-delta-carboxylic acid; Ethyl-2,4-dioxovalerate (Kg) is added to a solution of methyl hydrazine (L) in ethanol (L) and heated to 6O0C for 18 hours to provide the intermediate 3,5-dimethyl-pyrazole-5- carboxylic acid ethylester.

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 1,3-dimethyl-1H-pyrazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2006/48761; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1192-21-8, A common heterocyclic compound, 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, molecular formula is C4H7N3, 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.

in two screw-top glass pressure vessels, split and combine the following amounts in two equal portions 2-(2-chioro-4-pyridyi)-5-(2-nethoxyethyi)-6,6-dimethyi-thieno[2,3- c]pyrroi-4-one (13 g, 38.59 mmol), 1-methyi-5-aminopyrazole (11.245 g, 115.78 mmoi),cesium carbonate (37.724 g, 115.78 mrnol), 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (2.010 g, 3.47 mmoi), paiiadium(ii)acetate (520 mg, 2.32 nmoi) and 1,4-dioxane (350 mL). Seal each vessel and heat at 110 °C overnight.Dilute the reaction mixture with 10percent MeOH in DCM (2 L) and wash the resulting solution with saturated NaC1. Back extract the aqueous solution with DCM and combinethe organic solutions. Dry the combined solutions over a mixture of an hyous sodium sulfate and aithydrous magnesium sulfate, filter and concentrate the filtrate under reduced pressure. Purify by silica gel chromatography by loading the residue onto a 260 g loading coiunm with DCM and then eluting the loading coiunm onto a 750 g silica gel column with a gradient of 60-100percent of 10percent MeOH in EtOAc in hexane to yield the titlecompound 8.4 g (55percent). MS rn/z): 398 (M+i).

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; ELI LILLY AND COMPANY; CORTEZ, Guillermo S.; JOSEPH, Sajan; MCLEAN, Jonathan Alexander; MCMILLEN, William T.; RODRIGUEZ, Michael John; ZHAO, Gaiying; (70 pag.)WO2016/106009; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 89717-64-6, 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. 89717-64-6, name is 4-Bromo-3-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-bromo-3- nitro-lH-pyrazole (1.5 g, 7.8 mmol) in anhydrous THF (50 mL) was added phenylboronic acid (0.95 g, 7.8 mmol), copper(II) acetate (2.1 g, 11.7 mmol) and pyridine (2.5 g, 31.2 mmol. The mixture was stirred overnight at 40C under oxygen atmosphere. After removing the insolubles by filtration, the filtrate was diluted with EtOAc (50 mL), washed with water (50 mL) and brine (50 mL), dried over a2S04, filtered and concentrated in vacuo to obtain a residue which was purified by silica gel chromatography (eluting with hexane/EtOAc = 1/1) to afford 4-bromo-3-nitro-l -phenyl- lH-pyrazole as a yellow solid (2.0 g, Yield: 95%). ESI- LCMS (m/z): 268.0 [M+l]

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

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; (178 pag.)WO2016/44666; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 17635-44-8, name is 3,4,5-Tribromopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 17635-44-8

General procedure: 3,4,5-Tribromopyrazole (9a; 762 mg, 2.5 mmol) or 3,5-dibromo-4-nitropyrazole(9b; 677 mg, 2.5 mmol), o-quinone methide precursor 2(2.5 mmol) and K2CO3 (only for 9a, 1.035 g, 7.5 mmol) were refluxedfor 4 h in DMF (10 mL). Product was isolated analogously to compound4a.

The synthetic route of 17635-44-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Osipov, Dmitry V.; Osyanin, Vitaly A.; Voskressensky, Leonid G.; Klimochkin, Yuri N.; Synthesis; vol. 49; 10; (2017); p. 2286 – 2296;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 15878-00-9, name is 4-Chloro-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. Recommanded Product: 4-Chloro-1H-pyrazole

EXAMPLE 5 7.65 g (0.075 mole) of 4-chloropyrazole were suspended in 100 ml of water and the suspension obtained first had added to it 72 g (0.64 mole) of a 50% strength aqueous KOH solution and then at 0 C. 17 g (0.15 mole) of a 30% strength aqueous hydrogen peroxide solution. After the reaction mixture had been stirred for 5 minutes, 28 g (0.18 mole) of phthalic anhydride were added in small portions at 10 C., and the whole was stirred overnight and then worked up similarly to Example 1. Yield: 7.1 g of 4-chloro-N-hydroxypyrazole, corresponding to 80% of theory.

The synthetic route of 4-Chloro-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Basf Aktiengesellschaft; US4945167; (1990); A;,
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. 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H7N3O

Example 15To a solution of cyanuric chloride (300 mg, 1.63 mmol) in THF (16 mL) was added benzylmercaptan (0.19 mL, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 3-amino-5-(2- furyl)pyrazole (243 mg, 1.63 mmol) and DIPEA (0.21 mL, 1.63 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1 -methylpiperazine (0.36 mL, 3.26 mmol) and DIPEA (0.57 mL, 3.26 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 15 as white solid (250 mg, 34 %). 1H NMR (400 MHz, DMSOd6) delta 12.83 (s, 1H, NH), 9.92 (bs, 1Eta, NH), 7.74-6.59 (m, 9Eta, Ar-H), 4.34 (s, 2Eta, CH2), 3.75 (s, 4Eta, 2CH2), 2.34 (s, 4Eta, 2CH2), 2.29 (s, 3Eta, CH3); ESI-MS: calcd for (C22Eta24N8OS) 448, found 449 [M+H]+. HPLC: retention time: 20.34 min. purity: 99%.

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; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; HO, David; NALLAN, Laxman; POLAT, Tulay; SUN, Xiaowen; DESAI, Neil; WO2010/144394; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics