Category: 39806-90-1

Synthetic Route of 39806-90-1, The chemical industry reduces the impact on the environment during synthesis 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

To a solution of 4-iodo-1-methyl-1H-pyrazole (55 gm, 0.264 moles) in N,N-dimethylacetamide (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 90-110 C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30 C., to this added DI water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30 C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted with ethyl acetate (200 ml), stirred for 15 min 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 60-70 C. The mixture was degassed for 2 hour at reduced pressure at 60-70 C., cooled the mixture to 20-30 C. Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30 C. The solid product obtained was filtered off, washed with cold DI water (100 ml) and dried at 40-50 C. to yield the product, 1-methyl-1H-pyrazole-4-carbonitrile.

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-Iodo-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RALLIS INDIA LIMITED; Pawar, Jivan Dhanraj; Palimkar, Sanjay Sambhajirao; Sankar, B.; Kadam, Subhash Rajaram; Hindupur, Rama Mohan; Prabhu, Venkatesh M.; Pati, Hari Narayan; Suphala, Vadiraj Gopinath; Mane, Avinash Sheshrao; US2015/112063; (2015); 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

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

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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H5IN2

1-Methyl-4-((trimethylsilyl)ethynyl)-1 W-pyrazole (19); [00204] 1 -Methyl-4-iodo-pyrazole (18) (5.0g 24.04mmole) was dissolved in DMF (32ml_) and ethynyltrimethylsilane (4.76ml_, 3.31 g, 33.7mmole) was added followed by diisopropylamine (4.46ml_, 3.21 g 31 .78mmole), copper(l) iodide (304mg 1 .59mmole) and triphenylphosphine (1 .26g 4.81 mmole). The reaction was flushed with argon. Palladium acetate (351 mg 1 .56mmole) was added and the reaction was again flushed with argon. It was heated at 60C for 60 mins. The reaction was cooled, added to water (350ml) and extracted with ether (3x100ml_). The organic solution was filtered from a brown solid which was washed with a little more ether. The organic solution was washed with water (3x80ml_), brine, dried and evaporated. The crude product was flash chromatographed (silica) using 1 :4 ethyl acetate:cyclohexane and then 1 :3 ethyl acetate:cyclohexane to give the title compound as a solid (2.85g 67%). 1 H-NMR (CDCI3, 500MHz): delta 0.24 (s, 9H), 3.87 (s, 3H), 7.50 (s, 1 H), 7.58 (s, 1 H).

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 39806-90-1.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 39806-90-1,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.

Step 1: A clean and dry 500 L glass-lined reactor A was evacuated to -0.08–0.O5MPa and filled with nitrogen to normal pressure. It was repeated for 3 times. The reactors were sampled for oxygen content to ensure it was 3%.[001145j Diisopropylamine (106.0 kg) and 1-methyl-4-iodo-1H-pyrazole (24.3 kg, 23.6 kg corrected) were added to the reactor A at 15-25 C. Cuprous iodide (0.37 kg) was added to reactor A under the protection of nitrogen at 15-25 C. Bis(triphenylphosphine)palladium(II) chloride (1.09 kg) was added to the mixture under the protection of nitrogen at 15-25 C. The mixture was stirred for 20-30 mi Trimethylsilylacetylene (22.2 kg, 14.0 kg corrected) was added to the mixture in portions with 4-5 kg and an interval of 20-30 mm for each portion at 15-30 C. The mixture was allowed to react at 20-30 C. After 2h, the mixture was sampled every 1-2h for purity analysis by HPLC until area% of 1-methyl-4-iodo-1H-pyrazole was 0.5%.[001 146j After reaction completion, the mixture was filtered with a stainless steel centrifuge. The filter cake was rinsed twice with methyl tert-butyl ether (9.2 kg x2). The filtrate was transferred to reactor A and concentrated under reduced pressure (P -0.08 MPa) at T 45 C until 40-60 L was left. Methyl tert-butyl ether (92.5 kg) was added to the mixture and concentration was continued until 40-60 L was left. Methyl tert-butyl ether (92.2 kg) was added to concentrated mixture and the mixture was sampled for diisopropylamine residual analysis to ensure it was 1%. Active carbon (4.9 kg) was added to the mixture at 15-25 C and the mixture was maintained for 6-8 h under stirring. The mixture was filtered with stainless steel nutsche filter at 15-25 C. The filter cake was rinsed twice with methyl tert-butyl ether (9.2 kg x2). A solution of citric acid monohydrate (6.1 kg) in purified water (121.6 kg) was added to the filtrate at 15-25 C. The mixture was stirred for 20-30 mm and settled for 20-3 0 mm before separation. The emulsion layer was separated to aqueous phase. The aqueous phase was sampled for pH analysis and wt% analysis to ensure pH was < 7. Active carbon (4.9 kg) was added to the mixture at 15-25 C and the mixture was maintained for 6-8 h under stirring. The mixture was filtered with stainless steel nutsche filter at 15-25 C. The filter cake was rinsed twice with methyl tert-butyl ether (9.2 kg x2). The filtrate was checked to ensure it was yellow solution. The filtrate was transferred to reactor B and concentrated under reduced pressure (P -0.O8MPa) at T 35 C until 30-40 L was left. Anhydrous ethanol (96.3 kg) was added to the mixture and concentration was continued at T 45 C until 30-40 L was left. The mixture was sampled for methyl tert-butyl ether residual analysis to ensure it was 0.5%. The mixture was cooled to 15-25 C. Purified water (121.3 kg) was added to the mixture through peristaltic pump at 15-25 C at a reference rate of 25-50 kg/h. Brown yellow solid precipitated. The mixture was allowed to crystallize at 15-25 C. After 2h, the mixture was sampled every 1- 2h for mother liquor wt% analysis until it was 0.5% or the difference between the two samples was 0.3%. The mixture was filtered with a stainless steel nutsche filter. The filter cake was rinsed twice with purified water (12.1 kg x2). The filter cake was swept in the stainless steel nutsche filter. After 12h, the solid was sampled every 6-8h for ethanol residual until it was 1%. The product was packaged in one plastic bag. Product weight12.0 kg, Yield = 52.3%, Purity (HPLC) = 98.9%. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-1-methyl-1H-pyrazole, its application will become more common. Reference:
Patent; INFINITY PHARMACEUTICALS, INC.; CRENIER, Louis; LESCARBEAU, Andre; SHARMA, Praveen; GENOV, Daniel G.; (324 pag.)WO2017/48702; (2017); 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Iodo-1-methyl-1H-pyrazole

To a solution of 4-amino- 1 -methyl -pyrrolidin-2-one (100 mg, 0.88 mmol) in toluene (2 ml) was added 4-iodo- 1 -methyl-pyrazole (200 mg, 0.96 mmol), sodium tert-butoxide (168 mg, 1.75 mmol) and [2-(2-aminoethyl)phenyl]-chloro-palladium;ditert-butyl-[2- (2,4,6- triisopropylphenyl)phenyl]phosphane (also known as tBuXPhos Pd Gl) (60 mg, 88 pmol), then the mixture was stirred at 100 C for 3 h. The mixture was concentrated under reduced pressure. The residue was purified by prep-HPLC (column: Waters Xbridge Prep OBD C18 5pm 150×30; mobile phase: [water (0.1 % TFA) – ACN]; B: 1 – 30 %,l0 min) to give the title compound as colourless gum (Y = 20 %). ‘H NMR (400 MHz, methanol-*) d ppm 7.63 (s, 1H), 7.43 (s, 1H), 4.17 – 4.05 (m, 1H), 3.87 (s, 3H), 3.84 – 3.76 (m, 1H), 3.43 (dd, J= 3, 11 Hz, 1H), 2.90 – 2.79 (m, 4H), 2.41 (dd, j= 3, 18 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; NODTHERA LIMITED; HARRISON, David; WATT, Alan Paul; BOCK, Mark G.; (334 pag.)WO2019/121691; (2019); 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, Recommanded Product: 4-Iodo-1-methyl-1H-pyrazole

To a mixture of Cul (6 mg, 0.033 mmol, 0.2 equiv.), 4-iodo-l -methyl- 1H- pyrazole (41 mg, 0.195 mmol, 1.2 equiv.) and K2CO3 (90 mg, 0.651 mmol, 4.0 equiv.) were added methyl 3-((4-chlorobenzyl)amino)-2-oxopyrrolidine-3-carboxylate (46 mg, 0.163 mmol, 1.0 equiv.) in anhydrous l,4-dioxane (2 mL) and N,N-dimethylethylenediamine (4 m^, 0.033 mmol, 0.2 equiv.). The resulting mixture was flushed with nitrogen, sealed, heated in an oil bath at 115 C for 18 h, cooled to room temperature, filtered through a syringe filter, and purified with reverse phase HPLC using 10% – 100% ACN / water (both with 0.1% formic acid; Phenomenex Gemini C18 5 micron column) to provide 8 mg (14%) of methyl 3- ((4-chlorobenzyl)amino)-l-(l-methyl-lH-pyrazol-4-yl)-2-oxopyrrolidine-3-carboxylate. LRMS (APCI) m/z 363.2 (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; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; ASHCRAFT, Luke W.; LAU, Kevin; (455 pag.)WO2020/47447; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 39806-90-1, 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-iodo-l-methyl-lH-pyrazole (23.31 mg, 0.112 mmol) in anhydrous DMSO (5 ml) was added intermediate 19.6-2 (20 mg, 0.075 mmol), (Irans)-N 1.N2-dimethylcycloheane- 1, 2-diamine (2.125 mg, 0.015 mmol), potassium phosphate (47.6 mg, 0.224 mmol), and Cul (1.423 mg, 7.47 pmol). The resulting mixture was stirred at 90C under N2 protection for 12 hours. Afterward, the crude reaction solution was filtered and concentrated. The crude material was purified by pre-HPLC (TFA) to give example 19.7-2, ( R,R or 5riV)-5-chloro-6-(3-nuoro- 1 – methylpiperidin-4-yl)-l-(l-methyl-lH-pyrazol-4-yl)-lH-indazole, TFA salt. MS (ESI) m/z calc?d for Ci7H20ClFN5 [M+H]+ 348, found 348. NMR (400 MHz, CD3OD) d 8.12-8.22 (m, 2H), 7.94 (s, 1H), 7.87 (s, 1H), 7.66 (s, 1H), 5.22-5.48 (m, 1H), 3.75-4.03 (m, 5H), 3.60 (m, 1H), 3.15-3.31 (m, 1H), 3.15-3.31 (m, 1H), 3.03 (s, 3H), 2.26 (br s, 1H), 2.10 (m, 1H). LRRK2 IC50 3.0 nM.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; SIMOV, Vladimir; KAPLAN, William, P.; ACTON, John, J., III; ARDOLINO, Michael, J.; CHEN, Joanna, L.; FULLER, Peter, H.; GUNAYDIN, Hakan; LI, Derun; LIU, Ping; LOGAN, Kaitlyn Marie; METHOT, Joey; MORRIELLO, Gregori, J.; NEELAMKAVIL, Santhosh, F.; TORRES, Luis; YAN, Xin; ZHOU, Hua; (0 pag.)WO2020/92136; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 39806-90-1, 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 39806-90-1 as follows.

Example 58. Synthesis of (R)-5-(l,4-dimethyl-6-(l-methyl-lH-pyrazol-4-yl)-5,6- dihydro-4H-benzo[b] [l,2,4]triazolo[4,3-d][l,4]diazepin-8-yl)pyridin-2-amine (Compound 76). The title compound was synthesized by the following scheme:[00393] (R)-8-bromo-l,4-dimethyl-6-(l-methyl-lH-pyrazol-4-yl)-5,6-dihydro-4H-benzo[b] [l,2,4]triazolo[4,3-d][l,4]diazepine (Step 1). A mixture of (R)-8-bromo-l,4-dimethyl-5,6- dihydro-4H-benzo[b][l,2,4]triazolo[4,3-d][l,4]diazepine (292 mg, 1 mmol), 4-iodo-l-methyl- lH-pyrazole (312 mg, 1.5 mmol), copper (I) iodide (58 mg, 0.3 mmol), 1,10-phenanthroline (54 mg, 0.3 mmol) and potassium phosphate (424 mg, 2 mmol) in dimethyl sulfoxide (10 mL) was heated at 150C for 14 hours under nitrogen. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (20 mL x 3). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated to give (R)-8-bromo-l,4-dimethyl- 6-(l-methyl-lH-pyrazol-4-yl)-5,6-dihydro-4H-benzo[b] [1,2,4] triazolo[4,3-d][l,4]diazepine which was used in the next step without further purification. LRMS (M+H)+: calcd 372.07; found 372.

According to the analysis of related databases, 39806-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; GEHLING, Victor, S.; HEWITT, Michael, C.; TAYLOR, Alexander, M.; HARMANGE, Jean-Christophe; WO2012/151512; (2012); A2;,
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. Application In Synthesis of 4-Iodo-1-methyl-1H-pyrazole

To a solution of 4-iodo-1-methyl-pyrazole (2.68 g, 12.9 mmol) and tert- butyl piperazine-1 -carboxylate (2.00 g, 10.7 mmol) in /-PrOH (40 ml_), ethylene glycol (0.66 g, 10.7 mmol), Cul (0.41 g, 2.15 mmol) and K3P04 (9.12 g, 43.0 mmol) were added. The reaction mixture was heated in sealed tube at 100C for 20h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was concentrated in vacuo. The residue was diluted with H2O (150 ml_) and extracted with EtOAc (3 * 100 ml_). The organic layer was separated, washed with brine (100 ml_), dried over anhydrous Na2SC>4 and concentrated in vacuo. The crude residue obtained was purified by column chromatography (silica, 100-200 mesh, 0 to 2% MeOH in DCM) to afford tert-butyl 4-(1-methylpyrazol-4- yl)piperazine-1-carboxylate (0.93 g, 33%) as off-white solid. MS (ESI) m/e [M+H]7Rt/%: 267.00/2.45/82.5%. 1H NMR (400 MHz, CDCI3) 51.49 (s, 9H) 2.84 – 2.92 (m, 4H) 3.53 – 3.60 (m, 4H) 3.84 (s, 3H) 6.95 (s, 1 H) 7.21 (s, 1 H)

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; UCB BIOPHARMA SPRL; HALL, Adrian; (62 pag.)WO2018/138086; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics