Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 7119-95-1, name is 1-Nitropyrazole, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 7119-95-1, Recommanded Product: 7119-95-1

A solution of 1.0 g of N-nitropyrazole in 10 mL of benzonitrile was heated for 3 h at 180 °C, after cooling the reaction mixture was poured into 30 mL of hexane. 3-nitropyrazole was collected by filtration. The crude yield after washing with hexane and drying was 0.93 g (98percent). The solid was recrystallized from water. m.p. 174?175 °C. FT-IR (KBr, cm?1) 3180 (N?H), 1520 and 1351 cm?1 (NO2). 1H NMR (DMSO-d6) delta: 7.96 (d, 1, 5(3)-H), 6.96 (d, 1, 4-H). EI-MS: m/z 113 (M+·). Anal. Calcd for C3H3N3O2: C, 31.86; H, 2.67; N, 37.16. Found: C, 32.19; H, 2.84; N, 37.18.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Nitropyrazole, and friends who are interested can also refer to it.

Reference:
Article; Nageswara Rao; Ravi; Tewari, Surya P.; Venugopal Rao; Journal of Molecular Structure; vol. 1043; (2013); p. 121 – 131;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 153912-60-8, The chemical industry reduces the impact on the environment during synthesis 153912-60-8, name is 1,5-Dimethyl-1H-pyrazol-3-yl-methanol, I believe this compound will play a more active role in future production and life.

To a solution of (1 ,5-dimethyl-i H-pyrazol-3-yl)methanol (250 mg, 1.98 mmol) in CH2CI2 (15 mL) was added MesCI (0.16 mL, 2.08 mmol) and TEA (0.83 mL, 5.95 mmol). The reaction mixture was stirred at RT overnight, concentrated and the product used in the next step 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, 1,5-Dimethyl-1H-pyrazol-3-yl-methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige, Liliane, Jeanne; MAIBAUM, Juergen, Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan, Andreas; VULPETTI, Anna; WO2014/2054; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 14531-55-6, These common heterocyclic compound, 14531-55-6, name is 3,5-Dimethyl-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.

Step 1. Synthesis of 1-Benzyl-3,5-dimethyl-1H-pyrazol-4-amine (IA3a) To a solution of 3,5-dimethyl-4-nitropyrazole (IA1, 1.41 g, 10 mmol) in DMF (30 mL) were added benzyl bromide (IA2a, 2.05 g, 12 mmol) and Cs2CO3 (6.52 g, 20 mmol) and the mixture was allowed to stir at rt for 24 h. The reaction was quenched with water (50 mL) and the mixture was extracted with EtOAc. The organic phase was washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. After purification by flash column chromatography (0-50% EtOAc/hexanes), 1-benzyl-3,5-dimethyl-4-nitro-1H-pyrazole was obtained as a white solid (1.39 g, 60%). 1H NMR (CDCl3, 600 MHz) delta 7.37-7.28 (m, 3H), 7.16-7.12 (m, 2H), 5.26 (s, 2H), 2.56 (s, 3H), 2.55 (s, 3H). HRMS (ESI+) calcd for C12H14N3O2 (M+H)+ 232.1081, found 232.1079.

The synthetic route of 14531-55-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REGENTS OF THE UNIVERSITY OF MINNESOTA; Chen, Liqiang; Ai, Teng; (48 pag.)US2018/71258; (2018); 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 5334-40-7 as follows. Product Details of 5334-40-7

Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3-pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 h. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (1H NMR (400 MHz, DMSO-d6) D 14.4 (s, 1 H), 9.0 (s, 1 H), 4.4 (q, 2H), 1.3 (t, 3H)).

According to the analysis of related databases, 5334-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77428; (2006); 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. 3469-69-0, name is 4-Iodopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Iodopyrazole

Under an atmosphere of nitrogen a solution of 4-iodo-1H-pyrazole (1.58 g; 8.0 mmol) in anhyd. THF wasadded dropwise to a freshly prepared suspension of sodium hydride (0.21 g; 8.7 mmol). The reactionmixture was stirred for 3 h and then 1.0 mL of methyl iodide (2.24 g; 15.8 mmol) was added dropwise.The mixture was stirred for additional 12 h and quenched by adding approximately 50 mL of water. Thecrude product was extracted with Et2O and dried over sodium sulfate. After evaporation of the solvent theproduct was obtained as a yellowish solid. Yield: 1.64 g (98%)

The synthetic route of 3469-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ahlburg, Nils Lennart; Doppleb, Olivia; Hillrichs, Kai; Namyslo, Jan C.; Huebner, Eike G.; Schmidt, Andreas; Heterocycles; vol. 96; 7; (2018); p. 1203 – 1215;,
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. 13808-64-5, name is 4-Bromo-3-methylpyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

To a solution of 4-bromo-3-methyl-1H-pyrazole 1a (500 mg, 3.1 mmol) in 8 mL DMF was added NaH (60%purity, 149 mg, 6.2 mmol), ethyl 2-bromoacetate (570 mg, 3.4 mmol) and KI (489 mg, 2.9 mmol). The mixture was stirredat 80C for 12 h. To the reaction mixture was added H2O (20 mL), extracted with EA (20 mL*3), combined the organicphase, washed with H2O (20 mL*2), saturation NaCl solution (20 mL*2), dried over Na2SO4, filtered, the filtrate wasconcentrated under reduced pressure. The residue was purified by silica column chromatography (Eluent C) to give titleproduct ethyl 2-(4-bromo-3-methyl-1H-pyrazol-1-yl)acetate 1b (522 mg, pale yellow liquid), yield: 68.0%1H NMR (400 MHz, CDCl3) delta 7.44 (d, 1 H), 4.85 (s, 1H), 4.79 (s, 1H), 4.24 (q, 2 H), 2.23 (s, 3H), 1.29 (t, 3 H)

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; Medshine Discovery Inc.; Quingdao Huanghai Pharmaceutical Co., Ltd.; WU, Chengde; ZHANG, Zhiliu; YU, Tao; (125 pag.)EP3042907; (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. 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Safety of Ethyl 5-amino-1H-pyrazole-4-carboxylate

A mixture of ethyl 5-methyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1 ,5-a]pyrim idine-3-carboxylate (major isomer) and ethyl 8-methyl-6, 7-dihydro-5H-cyclopenta[d]pyrazolo[1 ?5-a]pyrimidine-3-carboxylate (minor isomer) (1 .28 g, 5.22 mmol, ratio of isomers ca 85/15) was stirred in a mixture of lithium hydroxide (26 ml, 26 mmol, 1 M aqueous solution), tetrahydrofuran (43 ml) and methanol (9.1 ml) for 3 days at room temperature. For work-up, aqueous hydrochloric acid (2 M) was added and the precipitate formed was collected byfiltration, washed with water and dried to yield the title compounds as mixture of isomers (ca10:1) (770 mg, 68percent).Maior isomer:[C-MS (Method 1): R = 0.71 mm; MS (ESIpos) m/z = 218.1 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 12.83-11.51 (br. s, 1H), 8.48 (5, 1H), 3.03 (t, 2H),2.55 (5, 3H), 2.30-2.21 (m, 2H).Minor isomer (characteristic sicinals ciiven):1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 8.45 (5, 1H), 3.00-2.95 (m, 2H), 2.68 (5, 3H), 2.20-2.10 (m, 2H). (benzotriazol-1 -yloxy)tripyrrolidinophosphonium hexafluorophosphate (172 mg, 0.331 mmol)was added to a mixture of 5-methyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1 ,5-a]pyrim idine-3-carboxylic acid (major isomer) and 8-methyl-6, 7-dihydro-5H-cyclopenta[d]pyrazolo[1 ?5- a]pyrimidine-3-carboxylic acid (minor isomer) (60.0 mg, 0.276 mmol, ratio of isomers: 10/1), trans-4-am ino-N-(2-chloro-4-f luorophenyl)cyclohexanecarboxam ide hydrochloride (76.4 mg, 0.249 mmol) and 192 hI (1.11 mmol) N-ethyl-N-isopropylpropan-2-amine in 2.0 ml N,N10 dimethylformamide and the mixture was stirred over night at room temperature. For work-up,water was added and the precipitate was collected by filtration, washed with water and dried under vacuum at 500 to provide the title compound (103 mg) together with its isomer N{trans-4-[(2-chloro-4-fluorophenyl)carbamoyl]cyclohexyl}-8-methyl-6,7-dihydro-5H-cyclopenta[d]pyrazolo[1 ,5-a]pyrimidine-3-carboxamide (ratios of isomers ca. 10/1 by 1 HNMR). The two isomers were separated by preparative HPLC [Instrument: Labomatic PumpeHD-5000, Labomatic SP-3000, Labocord 5000, Labomatic Labcol Vario 4000, Gilson GX241; Colum: Chiralpak IE Slim 250×30 mm Nr.027; Solvent: ethanol / methanol / diethylamine 50:50:0.1 (v/v/v), flow: 30 mI/mm; temperature: room temperature; MWD 254 nm] to give N-{trans-4-[(2-chloro-4-fluorophenyl)carbamoyl]cyclohexyl}-5-methyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1 ,5-a]pyrimidine-3-carboxamide (76.0 mg, 57percent yield). The minor isomer was not isolated in pure form.LC-MS (Method 2): R = 1 .23 mm; MS (ESIpos) m/z = 470.1 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 9.51 (br. s, 1H), 8.47 (5, 1H), 8.05 (d, 1H), 7.62(dd, 1H), 7.51 (dd, 1H), 7.23 (td, 1H), 3.87-3.72 (m, 1H), 3.40-3.36 (m, 2H), 3.07-3.01 (m,2H), 2.60 (5, 3H), 2.32-2.22 (m, 2H), 2.15-2.06 (m, 2H), 2.02-1.93 (m, 2H), 1.68-1.50 (m,2H), 1.47-1.32 (m, 2H).

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 PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (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. 14521-80-3, name is 3-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

1.1 Synthesis of Intermediates P Synthesis of 4-(1-(difluoromethyl)-1H-pyrazol-3-yl)-2, 6-difluorobenzaldehyde (P4) In a 150 mL pressure vessel, a suspension of 3-bromo-1H-pyrazole (8 g, 54.43 mmol) cesium carbonate (53.2 g, 163.29 mmol), and difluoroiodomethane (10% wt. in THF, 200 mL, 106.23 mmol) was heated at 45 C. overnight. The reaction mixture was cooled to room temperature and then filtered through Celite. The filter cake was washed with Et2O (3*150 mL). The filtrate was washed with brine, dried over sodium sulfate and carefully concentrated (20 C. bath, 100 mb vacuum) to give ?17 g of a 1.5:1 ratio of regioisomers and solvent still present. This crude material was combined with 3,5-difluoro-4-formylphenylboronic acid (12.65 g, 68.03 mmol), palladium acetate (0.31 g, 1.381 mmol), butyl di-1-adamantylphosphine (1.171 g, 3.265 mmol) and potassium carbonate (22.80 g, 164.96 mmol) in dioxane (150 mL) and water (50 mL) the mixture was degassed for 10 min with argon, then heated at 100 C. overnight. The reaction mixture was cooled to room temperature, concentrated under reduce pressure, the residue was diluted with EtOAc and washed with brine 2x then dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (5% to 15% EtOAc/Hex). Mixed fractions were recrystallized (5:1 Hex/EtOAc) and the combined pure product afforded P4. 1H NMR (400 MHz, Chloroform-d) delta 10.35 (d, J=1.0 Hz, 1H), 7.92 (d, J=2.8 Hz, 1H), 7.46 (d, J=9.6 Hz, 2H), 7.24 (t, J=60.5 Hz, 1H), 6.80 (d, J=2.8 Hz, 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; Gilead Sciences, Inc.; Chin, Elbert; Kato, Darryl; Link, John O.; Shapiro, Nathan; Yang, Zheng-Yu; (81 pag.)US2020/30327; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5203-77-0, 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. 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Intermediate 7 (4mmol), dissolved in dry dichloromethane (60mL), and PCl5 (4.2mmol) were added and stirred at room temperature for 1h. The solvent was moved out under reduced pressure to afford acid chloride, the acid chloride was then dissolved in dry CH2Cl2 (60mL), Then 1-methyl-1H-pyrazol-5-ol (4mmol) and Et3N (4.8mmol) were added to the above solution, and stirred for a further 18-24hat room temperature. After adding dichloromethane (30mL), the resultant mixture was washed sequentially with 2N hydrochloric acid (100mL), saturated NaHCO3 and saturated NaCl and dried over Na2SO4. The rest of the solution was evaporated in vacuum and purified by silica gel column chromatography using gradient elution of ethyl acetate/hexane (V:V = 1:2) to obtain the desired intermediate 8 as a write powder (30%-70%). 4.1.10 1-methyl-1H-pyrazol-5-yl3-methyl-2-oxo-1-propyl-2,3-dihydro-1H-benzo[d] imidazole- 5-carboxylate Yield: 45%. m.p. 107-108C. 1H NMR (600MHz, CDCl3) delta 8.01 (dd, J=8.4, 1.2Hz, 1H), 7.77 (d, J=1.2Hz, 1H), 7.48 (d, J=1.8Hz, 1H), 7.10 (d, J=8.4Hz, 1H), 6.20 (d, J=1.8Hz, 1H), 3.92 (t, J=7.2Hz, 2H), 3.80 (s, 3H), 3.51 (s, 3H), 1.91-1.71 (m, 2H), 1.00 (t, J=7.8Hz, 3H). EI-MS (m/z): 314.18 (M)+.

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, 1,3-Dimethyl-1H-pyrazol-5-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Yu-Ling; Lin, Hong-Yan; Ruan, Xu; Yang, Sheng-Gang; Hao, Ge-Fei; Yang, Wen-Chao; Yang, Guang-Fu; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 427 – 438;,
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. 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C4H3F3N2

Step A: Preparation of 2-chloro-4-[3-(trifluoromethyl)-lH-pyrazol-l-yl]benzaldehyde A mixture of 2-chloro-4-fluorobenzaldehyde (7.0 g, 44.3 mmol), 3-(trifluoromethyl)- lH-pyrazole (9.03 g, 66.45 mmol) and potassium carbonate (12.2 g, 88.6 mmol) in anhydrous N,N-dimethylformamide (70 mL) was stirred for 2 h at 110 °C. The reaction mixture was cooled to 0 °C, poured into ice water (800 mL) and stirred for 15 min. The precipitate formed was filtered and dried under reduced pressure to afford the title compound (10.2 g), which was used without further purification. H NMR delta 10.4 (s, 1H), 8.00 (m, 2H), 7.85 (d, 1H), 7.77 (m, 1H), 6.70 (d, 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; E. I. DU PONT DE NEMOURS AND COMPANY; BEREZNAK, James, Francis; TAGGI, Andrew, Edmund; MARCUS, Kimberly, Katherine; REDDY, Ravisekhara, P.; WO2014/172191; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics