Tag: M.W:200-300

Electric Literature of 92525-10-5, These common heterocyclic compound, 92525-10-5, name is 3-Iodo-1-methyl-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.

3-Iodo-1-methyl-1H-pyrazole (2.19 g, 10.5 mmol) was added dropwise to iPrMgCl.LiCl (10.8 mL, 14.0 mmol, 1.3 M THF solution) and THF (14 mL) cooled to 0 C. under a nitrogen atmosphere. The mixture was allowed to stir at room temperature for 1 h. N-Methoxy-N,1-dimethylcyclopentane-1-carboxamide (1.2 g, 7.0 mmol) was then added dropwise. The mixture was stirred at room temperature for 18 h and then was quenched with saturated aqueous NH4Cl. The reaction mixture was extracted with EtOAc. The organic extract was dried (Na2SO4) and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (10-50% EtOAc/heptane) to afford 992 mg (74%) of the title compound. LCMS 172.4 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.34 (d, J=2.3 Hz, 1H), 6.81 (d, J=2.3 Hz, 1H), 3.98 (s, 3H), 2.46-2.33 (m, 2H), 1.79-1.63 (m, 6H), 1.49 (s, 3H).

The synthetic route of 92525-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Gerstenberger, Brian Stephen; Flick, Andrew Christopher; Lombardo, Vincent Michael; Mousseau, James John; Nuhant, Philippe Marcel; Robinson, JR., Ralph Pelton; Schnute, Mark Edward; Kung, Daniel Wei-Shung; Schmitt, Daniel Copley; Thorarensen, Atli; Trujillo, John Isidro; Unwalla, Rayomand Jal; Wu, Huixian; (104 pag.)US2020/95239; (2020); 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. 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Iodo-1-methyl-1H-pyrazole

Step 1. Synthesis of 5-fluoro-3-iodo-1-methyl-1H-pyrazole (C27) Lithium diisopropylamide (2.0 M in heptane/tetrahydrofuran/ethylbenzene, 3.30 mL, 6.60 mmol) was added drop-wise to a -75 C. solution of 3-iodo-1-methyl-1H-pyrazole (97%, 1.29 g, 6.02 mmol) in tetrahydrofuran (25 mL). After 5 minutes, N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (97%, 2.60 g, 8.00 mmol) was added to the cold solution in one portion. The reaction mixture was allowed to warm to 0 C. over 30 minutes, and was then quenched with saturated aqueous ammonium chloride solution (25 mL) and extracted with ethyl acetate (3*30 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (15 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane) afforded the product as a pale yellow oil. Yield: 435 mg, 1.92 mmol, 32%. GCMS m/z 226 [M+]. 1H NMR (400 MHz, CDCl3) delta 5.93 (d, J=6.0 Hz, 1H), 3.74 (d, J=1.2 Hz, 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 92525-10-5.

Reference:
Patent; Pfizer Inc.; Brodney, Michael Aaron; Butler, Christopher Ryan; Beck, Elizabeth Mary; Davoren, Jennifer Elizabeth; LaChapelle, Erik Alphie; O’Neill, Brian Thomas; US2014/228356; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1202993-11-0, 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. 1202993-11-0, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Chloro-3-(difluoromethyl)- 1-methyl-i H-pyrazole-4-carboxylic acid (700 mg, 2.38 mmol) was dissolved in abs. dichioromethane (20 ml) in a baked-out round- bottom flask under argon and at room temperature, and oxalyl chloride (257 mg, 2.02 mmol) and catalytic amounts of N,N-dimethylformamide were added. The resulting reaction solution was then stirred under reflux conditions for 3 h. Afier cooling to room temperature, the reaction mixture was concentrated and coevaporated with a little abs. toluene.By thorough removal of solvent residues, 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride (743 mg, 2.38 mmol) was obtained, which was then, without further purification, dissolved again in abs. dichloromethane (10 ml) and added dropwise to a solution, cooled to 0 C., of N,N-dimethylhydrazine (0.18 ml, 2.38 mmol) and triethylamine (0.40 ml, 2.85 mmol) in dichloromethane (10 ml) under argon. The resulting reaction mixture was stirred at room temperature for a further 30 minutes, and then water and dichloromethane were added. The aqueous phase was repeatedly extracted vigorously with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification of the resulting crude product by column chromatography gave 5-chloro-3-(difluoromethyl) -N’,N’,1-trimethyl-1H-pyrazole-4-carbohydrazide in the form of a colorless solid (541 mg, 90% of theory). 5-Chloro-3-(difluoromethyl) -N?,N?,1 -trimethyl- iH-pyrazole-4-carbohydrazide (212 mg, 0.84 mmol) was dissolved in abs. tetrahydrofuran (5 ml) under argon, and sodium hydride (37 mg, 0.92 mmol, 60% purity) was added at room temperature. Stirring at room temperature for 30 minutes was followed by the addition of picolyl chloride (107 mg, 0.84 mmol), and the resulting reaction mixture was stirred under reflux conditions for 2 hours. After cooling to room temperature, sat. sodium hydrogencarbonate solution, water and dichioromethane were added. The aqueous phase was repeatedly extracted vigorously with dichioromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification of the resulting crude product by colunm chromatography gave 5-chloro-3-(difluoromethyl)-N?,N?, 1 -trimethyl-N-(pyridin-2-ylmethyl)- iH-pyrazole4-carbohydrazide in the form of a colorless solid (196 mg, 68% of theory). ?H-NMR (400 MHz, CDC13 oe, ppm) 8.64 (m, iH), 7.73 (m, iH), 7.63 (m, iH), 7.36 (m, iH), 7.15-6.88 (br. t, iH, CHF2), 5.11 (s, 2H), 3.86 (s, 3H), 3.48 (s, 6H).

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, 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer CropScience Aktiengesellschaft; FRACKENPOHL, Jens; BOJACK, Guido; BRUENJES, Marco; HELMKE, Hendrik; LEHR, Stefan; BRUECHNER, Peter; TIEBES, Joerg; MOSRIN, Marc; DITTGEN, Jan; SCHMUTZLER, Dirk; DESBORDES, Philippe; (92 pag.)US2018/206498; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 345637-71-0, The chemical industry reduces the impact on the environment during synthesis 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, I believe this compound will play a more active role in future production and life.

To a solution of (3-bromophenyl) (methyl)(((2-(piperidin-4-yl) thiazol-4-yl) methyl)imino)^6-sulfanone ; (362 mg, 0.9 mmol) in N, N-dimethylformamide (8 ml), N, N-diisopropylethylamine (0. 18 mi, 1.1 mmol) was added at 25 C. The resulting reaction mixture was stirred for 10 min, then (HATU (498 mg, 1.3 mmol) and 2-(5-methyl-3-(trifluoromethyl)- l H-pyrazoI- l -yl)acetic acid (200 mg, 1 .0 mmol) were added and stirred at 25 C for l h. The reaction was quenched with water ( 10 mL) then extracted twice with ethyl acetate ( 15mL), combined ethyl acetate layer was washed with brine ( 10 mL) and dried over sodium sulphate, concentrated and purified by preparative HPLC to obtain (3-bromophenyl)(methyl)(((2-( l -(2-(5- methyl-3-(trifluoromethyl)- l H-pyrazol- l -yI)acetyl)piperidin-4-yl)thiazol-4-yl)methyl)imino)-6- sulfanone ( 170 mg, 0.3 mmol, 32 % yield).

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, 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PI INDUSTRIES LTD.; SHANBHAG, Gajanan; SHARMA, Aditya; RENUGADEVI, G.; PABBA, Jagadish; DENGALE, Rohit Arvind; ROY, Dipankar; S.P., Mohan Kumar; BELKAR, Yogesh Kashiram; AUTKAR, Santosh Shridhar; GARG, Ruchi; VENKATESHA, Hagalavadi M; KLAUSENER, Alexander Guenther Maria; (114 pag.)WO2019/48988; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 92525-10-5, These common heterocyclic compound, 92525-10-5, name is 3-Iodo-1-methyl-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.

3-Iodo-1-methyl-1H-pyrazole (2.19 g, 10.5 mmol) was added dropwise to iPrMgCl.LiCl (10.8 mL, 14.0 mmol, 1.3 M THF solution) and THF (14 mL) cooled to 0 C. under a nitrogen atmosphere. The mixture was allowed to stir at room temperature for 1 h. N-Methoxy-N,1-dimethylcyclopentane-1-carboxamide (1.2 g, 7.0 mmol) was then added dropwise. The mixture was stirred at room temperature for 18 h and then was quenched with saturated aqueous NH4Cl. The reaction mixture was extracted with EtOAc. The organic extract was dried (Na2SO4) and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (10-50% EtOAc/heptane) to afford 992 mg (74%) of the title compound. LCMS 172.4 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.34 (d, J=2.3 Hz, 1H), 6.81 (d, J=2.3 Hz, 1H), 3.98 (s, 3H), 2.46-2.33 (m, 2H), 1.79-1.63 (m, 6H), 1.49 (s, 3H).

The synthetic route of 92525-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Gerstenberger, Brian Stephen; Flick, Andrew Christopher; Lombardo, Vincent Michael; Mousseau, James John; Nuhant, Philippe Marcel; Robinson, JR., Ralph Pelton; Schnute, Mark Edward; Kung, Daniel Wei-Shung; Schmitt, Daniel Copley; Thorarensen, Atli; Trujillo, John Isidro; Unwalla, Rayomand Jal; Wu, Huixian; (104 pag.)US2020/95239; (2020); 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. 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Iodo-1-methyl-1H-pyrazole

Step 1. Synthesis of 5-fluoro-3-iodo-1-methyl-1H-pyrazole (C27) Lithium diisopropylamide (2.0 M in heptane/tetrahydrofuran/ethylbenzene, 3.30 mL, 6.60 mmol) was added drop-wise to a -75 C. solution of 3-iodo-1-methyl-1H-pyrazole (97%, 1.29 g, 6.02 mmol) in tetrahydrofuran (25 mL). After 5 minutes, N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (97%, 2.60 g, 8.00 mmol) was added to the cold solution in one portion. The reaction mixture was allowed to warm to 0 C. over 30 minutes, and was then quenched with saturated aqueous ammonium chloride solution (25 mL) and extracted with ethyl acetate (3*30 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (15 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane) afforded the product as a pale yellow oil. Yield: 435 mg, 1.92 mmol, 32%. GCMS m/z 226 [M+]. 1H NMR (400 MHz, CDCl3) delta 5.93 (d, J=6.0 Hz, 1H), 3.74 (d, J=1.2 Hz, 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 92525-10-5.

Reference:
Patent; Pfizer Inc.; Brodney, Michael Aaron; Butler, Christopher Ryan; Beck, Elizabeth Mary; Davoren, Jennifer Elizabeth; LaChapelle, Erik Alphie; O’Neill, Brian Thomas; US2014/228356; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-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. Application In Synthesis of Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate

To lambda/-(5-(chloromethyl)-2,3-dihydro-7/-/-inden-1-yl)propane-2-sulfonamide (0.250 mmol, 72 mg) in DMF (4 ml.) was added ethyl 3-(trifluoromethyl)-7/-/-pyrazole-4-carboxylate (0.250 mmol, 52.1 mg) and Potassium carbonate (0.750 mmol, 104 mg). The resultant solution was heated to 60 0C with stirring. After 1.5 h the reaction mixture was concentrated to remove DMF before partitioning between EtOAc/H2O and the phases mixed and separated. The organic layer was washed with water (x 4) and brine before drying and concentration to a yellow oil. Purification on 10g Si eluting with 1% MeOH/DCM gave the desired compound as an off-white solid (60 mg, 0.131 mmol, 52.2 %). 1H NMR (400 MHz, CDCI3) delta 1.33 (t, 3H) 1.44 (d, 6H) 1.95 (m, 1 H) 2.65 (m, 1 H) 2.85 (m, 1 H) 3.00 (m, 1 H) 3.25 (m, 1 H) 4.15 (d, 1 H) 4.29 (q, 2H) 4.95 (m, 1 H) 5.30 (s, 2H) 7.14 (s, 1 H) 7.18 (d, 1 H) 7.48 (d, 1 H) 7.88 (s, 1 H).

The synthetic route of 155377-19-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2009/147167; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, molecular formula is C4H5IN2, 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. COA of Formula: C4H5IN2

Step 2: I-methyl-IH-pyrazole-4-carbonitrileTo a solution of 4-iodo-I-methyl-IH-pyrazole (55 gm, 0.264 moles) in N,Ndimethylacetamide (100 ml) was added potassium ferrocyanide (24.5 gm, 0.058 moles),palladium (II) acetate (0.592 gm, 0,0026 moles) and sodium carbonate (27.98 gm, 0.264 moles). The reaction mixture was evacuated and backfilled with nitrogen (3 times). The mixture was stirred for 12 hour at 90-1 10C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30C, to this added Dl water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30 C. The reaction mixture was filtered throughpad of celite. The organic layer was separated and aqueous layer was extracted with ethyl acetate (200 ml), stirred for 15 mm and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70C. The mixture was degassed for 2 hour at reduced pressure at 60- 70C, cooled the mixture to 20-30C. Hexane (400 ml) was added to the mixture and stirredfor 1 hour at 20-30C. The solid product obtained was filtered off, washed with cold Dl water (100 ml) and dried at 40-50C to yield the product, 1-methyl-IH-pyrazole-4-carbonitrile,.? Drywt 17.94gmYield 0.32 w/w (63%);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39806-90-1, its application will become more common.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2110; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5932-30-9, A common heterocyclic compound, 5932-30-9, name is Ethyl 5-phenyl-1H-pyrazole-3-carboxylate, molecular formula is C12H12N2O2, 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.

To a solution of compound 23 (l.08g, 5.00 mmol) and compound 25 (981 mg, 6.00 mmol) in 50 ml acetonitrile was added K2CO3 (1.24 g, 9.00 mmol) and heated to reflux for 8 hours. After cooled to rt, filtered off, the filtrate was concentrated and the residue was purified by silica-gel column chromatography to afford compound 24a (950 mg, 55% yield) and compound 24b (150 mg, 8.7% yield).(compound 24a)LCMS m/z=344 [M+H]+ LC/MS informationColumn: Xbridge C18 (3.5pm 4.6x50mm)Flow rate: 1.8 mL/min UV detection wavelength: 254nmMobile phase’- [A] is 0.05% TFA-containing aqueoous solution, and [B] is 0.05% TFA- containing acetonitrile solutionFrom 0 to 1.5 minutes, the percentage of [B] in the mobile phase was gradually increased from 5% to 100%. Thereafter a solution of 100% of [B] was used as the mobile phase.retention time= 1.41 minutes.(compound 24b)LCMS m/z=344 [M+H]+ LC/MS informationColumn: Xbridge C18 (3.5mu?iota 4.6x50mm)Flow rate: 1.8 mL/minUV detection wavelength: 254nmMobile phase: [A] is 0.05% TFA-containing aqueoous solution, and [B] is 0.05% TFA- containing acetonitrile solutionFrom 0 to 1.5 minutes, the percentage of [B] in the mobile phase was gradually increased from 5% to 100%.. Thereafter a solution of 100% of [B] was used as the mobile phase.retention time= 1.50 minutes

The synthetic route of 5932-30-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; YUKIMASA, Akira; WO2012/144661; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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, Safety of 4-Iodo-1-methyl-1H-pyrazole

EXAMPLE 7; rac-3 -[(/ ?,2J?)-2-Hydroxycyclohexyl] -6- { [4-( 1 -methyLiH-pyrazol-4-yl)-3-oxopiperazin- 1 – yl] methyl } benzo [h] quinazolin-4(JH)-oneSynthesis of l-(l-methyl-7H-pyrazol-4-yl)piperazin-2-one.To a solution of /eri-bulyl 3-oxopiperazine-l-carboxylate (0.164 g, 0,819 mmol) in 3 mL of isopropanol under an atmosphere of nitrogen was added l-methyI-4-iodo-/H-pyrazole (0.204 g, 0.983 mmol), ethylene glycol (0.051 g, 0.82 mmol), copper iodide (0.031 g, 0.16 mmol), and potassium phosphate (0.695 g, 3.28 mmol). The reaction was heated to 100C for 8 h; cooled to rt, and concentrated in vacuo. The residue was dissolved in dichloromethane, washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 10-100% ethyl acetate in hexanes to provide tert- butyl 4-(l-methyl-7H-pyrazol-4-yl)-3-oxopiperazine-l-carboxylate that gave a mass ion (ES+) of 281.1 for [M+H .

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; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; BESHORE, Douglas, C.; DIMARCO, Christina, Ng; GRESHOCK, Thomas, J.; WO2011/84371; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics