Day: August 9, 2021

Adding a certain compound to certain chemical reactions, such as: 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, 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 39806-90-1, Recommanded Product: 39806-90-1

A mixture of 2-(3-{3-[5-benzyloxy-2-ethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenoxy]propoxy}-2-propylphenoxy)benzoic acid methyl ester (1.00 g, 1.47 mmol), 4-iodo-1-methylpyrazole (450 mg, 2.16 mmol), cesium carbonate (1.20 g, 3.62 mmol), and PdCl2(dppf) (72 mg, 0.088 mmol) in de-oxygenated toluene (35 mL) was heated at 100 C. for 24 h. Additional portions of 4-iodo-1-methylpyrazole (~30 mg) and PdCl2(dppf) (~30 mg) were added and heating continued at 100 C. for 40 h. The mixture was cooled to room temperature, concentrated in vacuo, diluted with methylene chloride, and filtered down a short plug of silica gel. The filtrate was concentrated in vacuo. Chromatography (silica gel, 35% ethyl acetate/65% hexane to 65% ethyl acetate/35% hexane) of the residue provided 710 mg (76%) of the title compound. 1H NMR (CDCl3) delta 7.86 (dd, J=8, 2 Hz, 1H), 7.80 (s, 1H), 7.69 (s, 1H), 7.37 (m, 6H), 7.28 (s, 1H), 7.09 (d, J=9 Hz, 1H), 7.04 (d, J=9 Hz, 1H), 6.78 (d, J=9 Hz, 1H), 6.67 (d, J=9 Hz, 1H), 6.56 (s, 1H), 6.42 (d, J=8 Hz, 1H), 5.08 (s, 2H), 4.18 (t, J=6 Hz, 2H), 4.15 (t, J=6 Hz, 2H), 3.85 (s, 3H), 3.81 (s, 3H), 2.63 (t, J=8 Hz, 2H), 2.59 (q, J=7 Hz, 2H), 2.30 (quintet, J=6 Hz, 2H), 1.55 (hextet, J=8 Hz, 2H), 1.23 (t, J=7 Hz, 3H), 0.89 (t, J=7 Hz, 3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Eli Lilly and Company; US6797723; (2004); B1;,
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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Methyl-4-nitro-1H-pyrazole

A solution of 940 mg (2.90 mmol) tert-butyl 4-[(5-methyl-4-nitro-1 H-pyrazol-1 – yl)methyl]piperidine-1 -carboxylate and tert-butyl 4-[(3-methyl-4-nitro-1 H-pyrazol-1 – yl)methyl]piperidine-1 -carboxylate (intermediate 17B) in 5 mL dichloromethane was stirred with 2.2 mL (29.0 mmol) trifluoroacetic acid for three hours. The reaction mixture was filtered over NH2 derivatized silica gel, and the filtrate was evaporated yielding 557 mg of the desired title compounds as crude product which was used without further purification. 1 H NMR (400 MHz, DMSO d6): delta (ppm) = 1.04 / 1.11 (m, 2H), 1.39 (m, 2H), 1.89 (m, 1 H), 2.38 (m, 2H), 2.42 / 2.60 (s, 3H), 2.90 (m, 2H), 3.95 / 4.01 (d, 2H), 8.80 / 8.23 (s, 1 H).

According to the analysis of related databases, 5334-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHMANN, Bernd; HEISLER, Iring; MUeLLER, Thomas; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (194 pag.)WO2016/12474; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 175277-11-9, 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. 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of 6-(2-amino-5-chlorothiazol-4-yl)-3,4-dihydroquinolin-2(1H)-one (0.200 g, 0.82 mmol) and 3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxylic acid (0.164 g, 0.96 mmol), and pyridine (0.32 mL, 4 mmol) in acetonitrile (5 mL) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.13 m L, 2.04 mmol). The sealed tube was heated to 100 C. for 16 h and the precipitation formed. After cooling, the precipitate was collected by filtration and washed with cold 1:1 acetonitrile/water to give 3-(tert-butyl)-1-methyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)-1H-pyrazole-5-carboxamide (0.216 g, 65%). 1H NMR (400 MHz, DMSO-d): delta 12.60 (bs, 1H), 10.19 (s, 1H), 7.75 (m, 1H), 7.71 (dd, 1H, J=8.4, 2.0 Hz), 7.53 (s, 1H), 7.33 (s, 1H), 6.91 (d, 1H, J=8.0 Hz), 4.09 (s, 3H), 2.94 (t, 2H, J=7.2 Hz), 2.48 (partial masked under d-DMSO, m, 2H), 1.27 (s, 9H). MS (ESI): Calcd. for C21H23N5O2S: 409, found 410 (M+1)+.

The synthetic route of 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nantbio, Inc.; Tao, Chunlin; Nallan, Laxman; Ho, David G.; Wang, Qinwei; Weingarten, Paul; Juncker-Jensen, Anna B.; (121 pag.)US2018/201610; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 92933-47-6, 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 92933-47-6 as follows.

To an ice-bath and stirred solution of fuming HNO3 (700.00 mg, 11.11 mmol, 0.5 mL, 1.71 eq) and fuming H2SO4 (1.88 g, 18.76 mmol, 1.02 mL, 98% purity, 2.89 eq) was added 3-isopropyl- lH-pyrazole-5-carboxylic acid (1 g, 6.49 mmol, 1 eq) in portionwise at 0 C over 5 min. After addition, the mixture was stirred at this temperature for 1 h then at 100 C for 6 h. LC-MS showed the starting material was consumed completely and one main peak with desired MS was detected. The mixture was poured into ice-water (30 g), the white precipitate was filtered and dried to yield 3-isopropyl-4-nitro-1H-pyrazole-5-carboxylic acid (700 mg, 3.20 mmol, 49.36% yield, 91.1% purity) as a white solid. MR (400 MHz, CD3OD) delta ppm 3.56 (spt, J = 7.0 Hz, 1H), 1.35 (d, J = 7.1Hz, 6H); ES-LCMS m/z 200.1 [M+H].

According to the analysis of related databases, 92933-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KYN THERAPEUTICS; CASTRO, Alfredo C.; EVANS, Catherine Anne; (632 pag.)WO2018/195397; (2018); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 155377-19-8, 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. 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 54; 2-(2-(4-(dimethylamino)methyl)-3-(trifluoromethyl)pyrazol-1-yl)acetamido)-4, 5,6,7- tetrahydrobenzof/?1thiophene-3-carboxamidea) (3-(trifluoromethyl)-7H-pyrazol-4-yl)methanolEthyl 3-(trifluoromethyl)-1 H-pyrazole-4-carboxylate (5.00 g, 24 mmol) was dissolved in dry THF (5OmL). LiAIH4 (912 mg, 24.4 mmol) was added portionwise with care. The reaction mixture was stirred at RT for 3 h. MeOH (50 mL) was added dropwise and stirring continued for 30 min before concentrating in vacuo to give an off white solid. EtOAc (50 mL) was added and the solid was stirred for 30 min before filtering. The filtrate was concentrated and this procedure was repeated 4 times before the filtrates, after concentration in vacuo, were combined and purified by flash column chromatography (silica gel; eluent EtOAc: heptane, 4:1) to give the desired product (2.1 g, 12.6 mmol, 53%).1 H NMR (400MHz, CD3OD): delta 4.65 (s, 2H), 7.63 (s, 1 H)

The synthetic route of Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate 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

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. 2075-46-9, name is 4-Nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., name: 4-Nitro-1H-pyrazole

Add 4-nitropyrazole (5g), K2CO3 (9.17g) to a 100mL eggplant-shaped bottle,2-bromoethyl methyl ether (7.38g),KI (1.47g) and 63mL CH3CN, reflux overnight.At the end of the reaction, spin dry under reduced pressure, add H2O 75mL, EA 50mL × 3, combine the organic layers, wash with saturated brine, and dry the organic phase with anhydrous Na2SO4.Dry under reduced pressure to give an oily product.

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; China Pharmaceutical University; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Zhang Dayong; Zhang Tiantai; Yin Yuan; Chen Chengjuan; Yu Runan; Shu Lei; (38 pag.)CN110885331; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 632365-54-9, 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 632365-54-9 as follows.

Step d: To a solution of methyl 5-amino-1 H-pyrazole-3-carboxylate (75 mg; 0.53 mmol) in DMF (2 mL) was added the 2-bromo-2-cyclohexyl-1-(4-fluorophenyl)ethanone ( 170 mg; 0.58 mmol) followed by potassium carbonate (263 mg; 2.66 mmol) and the reaction mixture was stirred at 75C. After 2 hours water (25 mL) was added and the aqueous layer was extracted with EtOAc (3 x 30 mL). The combined organics were washed with brine (25 mL), dried (MgS04) and concentrated to leave a brown oil (89 mg). The residue was redissolved in EtOH ( 2 mL) and 2M sulphuric acid (0.5 mL) was added and the reaction mixture was stirred at 70 C. After 2 hours NaHC03 (25 ml) was added and the aqueous layer was extracted with EtOAc (3 x 30 mL). The combined organics were washed with brine (25 mL), dried (MgS04) and concentrated to leave a brown oil (75 mg). Purification by reverse phase LCMS: Acetonitrile/water (0.1 % formic acid) afforded methyl 3-cyclohexyl-2-(4-fluorophenyl)- 1 H-imidazo[1 ,2-b]pyrazole-6-carboxylate (i) (8.5 mg) as an amorphous white solid. ESI-MS m/z calculated for [M+H]+: 342.16; found: 342.09.

According to the analysis of related databases, 632365-54-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOTA SCIENTIFIC MANAGEMENT PTY LTD; FREY, Barbara; HUFTON, Richard; HARDING, Michael; DRAFFAN, Alistair George; WO2013/36994; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 3398-16-1, The chemical industry reduces the impact on the environment during synthesis 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, I believe this compound will play a more active role in future production and life.

4-Bromo-3,5-dimethylpyrazole (3.5714 g, 20 mmol, 98%, 1.0 eq.) was added sequentially to a dry three-neck flask with a magnetic rotor.Phenylboronic acid (2.9552g, 24mmol, 99%, 1.2 equivalents),Palladium acetate (0.1123 g, 0.5 mmol, 0.025 equivalent),Ligand S-Phos (0.5027 g, 1.2 mmol, 98%, 0.06 equivalents),1,4-Dioxane (60 mL) and potassium carbonate (8.2920 g, 60 mmol, 3.0 eq.)Aqueous solution (20 mL). nitrogenAir bubbling for 15 minutes,The reaction vial was then placed in a 115 C oil bath.After stirring for 15 hours,The reaction was monitored by thin layer chromatography.Cool to room temperature,Extract with dichloromethane (20 mL x 3).Combine all organic phases,Dry over anhydrous sodium sulfate.Filtered, concentrated,The crude product was purified by flash chromatography on silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 3/1 to 1/2) to give 3,5-dimethyl-4-phenylpyrazole, white The solid was 3.0773 g, and the yield was 89%.

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, 4-Bromo-3,5-dimethylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang University of Technology; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Li Guijie; Feng Qi; Dai Jianxin; Zhao Xiangdong; Chen Shaohai; She Yuanbin; (64 pag.)CN109608506; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 5071-61-4, These common heterocyclic compound, 5071-61-4, name is 5-Phenyl-1H-pyrazole-3-carboxylic acid, 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 2B: Synthesis of l-(5-phenyl-lH-pyrazole-3-carbonyl)-N-(pyrimidin-2-yl)- N-{[2-(trimethylsilyl)ethoxy]methyl}-2,3-dihydro-lH-indole-5-sulfonamide 37.1 [00464] DIPEA (0.16 ml, 0.89 mmol) and HATU (170mg, 0.45 mmol) were added at rt to a stirred solution of 5 -phenyl- lH-pyrazole-3-carboxylic acid (60mg, 0.30 mmol) in DMF (HPLC grade, 10ml) followed by N-(pyrimidin-2-yl)-N-{[2-(trimethylsilyl)ethoxy]methyl}-2,3-dihydro- lH-indole-5 -sulfonamide (34.1, 120mg, 0.30 mmol). The mixture was stirred for 27h at rt then re-treated with 5 -phenyl- lH-pyrazole-3-carboxylic acid (30mg, 0.15 mmol), DIPEA (0.20 ml, 1.1 mmol) and HATU (220mg, 0.58 mmol) and stirred for 74h at rt. The solvent was removed in vacuo and the crude product purified by prep HPLC (MeCN/Water, 2mM ammonium bicarbonate) to afford 46mg (27%) of 1 -(5 -phenyl- lH-pyrazole-3 -carbonyl)-N-(pyrimidin-2-yl)- N-{[2-(trimethylsilyl)ethoxy]methyl}-2,3-dihydro-lH-indole-5-sulfonamide 37.1 as an off-white solid.

The synthetic route of 5071-61-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAZE THERAPEUTICS, INC.; SAIAH, Eddine; (148 pag.)WO2016/40449; (2016); 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 176969-34-9 as follows. SDS of cas: 176969-34-9

anti-Enriched 5-amino-9-isopropyl-benzonorbornene (42g, syn/anti-ratio 3:7; prepared as described in WO 04/35589 or WO 06/37632) was chromatographed on silica gel (2.1kg ) in ethyl acetate-hexane-(1:7). The last eluting fractions with antf-contents > 97% (1.2 g, g.l.c) were combined and rechromatographed on silica gel (25Og) in ethyl acetate to give 0.72g (1.96%) of a crystalline solid (m.p. 64 0C) with an antf-content of 99.2% (g.l.c).5-Amino-9-anNo.-isopropyl-benzonorbornene (0.72g, 99.2% anti, prepared as described above) was reacted with 5-difluoromethyl-2-methyl-pyrazole-4-carboxylic acid (0.76g, 1.2 eq.)tau bis-(2-oxo-3-oxazolidinyl)-phosphinic acid chloride (1.Og, 1.2 eq.) and triethylamine (0.87g, 2.4 eq.) in dichloromethane (25ml) at room temperature for 3h to give after aqueous work up with saturated NaHCO3-solution and purification on silica gel in ethyl acetate-hexane-(1 :2 ) a viscous oil. Crystallization from hexane afforded the desired product (1.18g, yield: 91.7%, m.p. 140 0C, 99.4% anti (g.l.c)). The crystalline material was analyzed by differential scanning calorimetry and x-ray diffraction and was identified as crystal modification I of anti-3-difluoromethyl-1-methyl-1 H-pyrazole-4- carboxylic acid (9-isopropyl-1 ,2,3,4-tetrahydro-1 ,4-methano-naphthalen-5-yl)-amide no presence of other crystalline forms was detected (see figures 4, 5 and 6).

According to the analysis of related databases, 176969-34-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA LIMITED; SYNGENTA PARTICIPATIONS AG; WO2008/113447; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics