Day: June 4, 2021

Adding a certain compound to certain chemical reactions, such as: 3469-69-0, name is 4-Iodopyrazole, 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 3469-69-0, category: pyrazoles-derivatives

General procedure: To a solution of pyrazole 1-13 (1 equiv.) and trifluoroacetic acid (0.01 equiv.) in dichloromethane(for 1 mol of pyrazole – 1 L of dichloromethane were used) ethyl vinyl ether (1.27 equiv.) wasadded dropwise, keeping the temperature between 28-32 C (exothermic reaction) and left to stir atroom temperature for 12-78 hours. Dichloromethane was washed with saturated NaHCO3 solution(1 × 250 mL – for 1 L of dichloromethane) then with deionized H2O (1 × 250 mL). Organic layerwas dried with anhydrous Na2SO4, and evaporated under reduced pressure. Products were purifiedby distillation or recrystallization.

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-Iodopyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mazeikaite, Rita; Sudzius, Jurgis; Urbelis, Gintaras; Labanauskas, Linas; ARKIVOC; vol. 2014; 6; (2014); p. 54 – 71;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 10010-93-2, The chemical industry reduces the impact on the environment during synthesis 10010-93-2, name is 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

[0151] To a solution of 5-methyl-3-(trifluoromethyl)-lH-pyrazole (6.0 g, 30 mmol, 1 eq) in CH3CN (60 mL), were added I2 (7.6 g, 30 mmol, 1 eq) and CAN (8.22 g, 15 mmol, 0.5 eq) in one portion. Then the mixture was stirred at room temperature overnight. TLC indicated the reaction was completed. The reaction mixture was poured into ice water and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (3×40 mL), aq.Na2S03 (2×30 mL), dried over Na2S04 and concentrated in vacuum to give crude product, which was purified by column chromatography on silica gel to give4-iodo-5-methyl-3- (trifluoromethyl)-lH-pyrazole (5.0 g, yield: 60.6%); LC/MS: m/z (M++l) = 277.

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, 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMARESOURCES (SHANGHAI) CO., LTD.; CHEN, Ping; ZHOU, Ding; SHAO, Shaoping; CAI, Zhen-wei; WO2013/6792; (2013); 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. 17635-44-8, name is 3,4,5-Tribromopyrazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 17635-44-8

To a solution of 3,4,5-tribromo-1H-pyrazole (25 g, 81.96 mmol, 1.0 eq) in THF (300 ml), was added n-BuLi (2.5 M in hexanes, 65.6 ml, 164 mmol, 2.0 eq) over 30 min at -78 C. and the RM was stirred at this temperature for 30 min. The RM was quenched by the dropwise addition of MeOH-THF (2:3; 125 ml) at -78 C., and stirred for an additional 1.5 h while gradually allowing it to warm to RT. The solvent was removed under reduced pressure. The residue was diluted with diethyl ether (600 ml), washed with aq. HCl (0.5 N, 60 ml) and brine (75 ml), dried (Na2SO4), filtered and concentrated under reduced pressure to afford the title product (16 g, 86%)

According to the analysis of related databases, 17635-44-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; Schunk, Stefan; Reich, Melanie; Koenigs, Rene Michael; (62 pag.)US2017/101397; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2075-46-9, name is 4-Nitro-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 2075-46-9, HPLC of Formula: C3H3N3O2

Step 1: Preparation of 3-chloro-1H-pyrazol-4-amine hydrochloride Into a 2 L three-necked round bottom flask affixed with an overhead stirrer, a temperature probe, an addition funnel, and a nitrogen inlet were added ethanol (600 mL) and 4-nitro-1H-pyrazole (50.6 g, 447 mmol). To this solution was added, in one portion, conc. HCl (368 mL) (note: rapid exotherm from 15 C. to 39 C.) and the resulting mixture was purged with nitrogen for 5 minutes. Palladium on alumina (5% w/w) (2.6 g, Alfa, black solid) was added to the mixture and stirred at room temperature while triethylsilane (208 g, 1789 mmol) was added drop-wise over 4 h. The reaction, which started to slowly exotherm from 35 C. to 55 C. over 2.0 h, was stirred for a total of 16 h and vacuum filtered through a plug of Celite to give a biphasic mixture. The mixture was transferred to a separatory funnel, the bottom aqueous layer was collected and rotary evaporated (60 C., 50 mmHg) to dryness with the aid of acetonitrile (3*350 mL). The resulting yellow solid was suspended in acetonitrile (150 mL) and allowed to stand for 2 h at room temperature followed by 1 h at 0 C. in the refrigerator. The solids were filtered and washed with acetonitrile (100 mL) to afford the titled compound 3-chloro-1H-pyrazol-4-amine hydrochloride (84 g, 97% yield, 80% purity) as a white solid: mp 190-193 C.; 1H NMR (400 MHz, DMSO-d6) delta 10.46-10.24 (bs, 2H), 8.03 (s, 0.54H), 7.75 (s, 0.46H), 5.95 (bs, 1H)); 13C-NMR (101 MHz, DMSO) delta 128.24, 125.97, 116.71.

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; DOW AGROSCIENCES LLC; Buysse, Ann M.; Niyaz, Noormohamed M.; Demeter, David A.; Zhang, Yu; Walsh, Martin J.; Kubota, Asako; Hunter, Ricky; Trullinger, Tony K.; Lowe, Christian T.; Knueppel, Daniel; Patny, Akshay; Garizi, Negar; LePlae, JR., Paul Renee; Wessels, Frank; Ross, JR., Ronald; DeAmicis, Carl; Borromeo, Peter; US2013/288893; (2013); 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. 7119-95-1, name is 1-Nitropyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 7119-95-1

A solution of 1-nitro-1H-pyrazole (4.00 g, 35.4 mmol) in 40 mL of benzonitrile was refluxed for 2 h. After being cooled to 25° C., the mixture was poured into 160 mL of hexanes. A white solid precipitated which was filtered and dried in vacuo, to afford 3-nitro-1H-pyrazole (3.16 g, 79percent). H1-NMR (400 MHz, DMSO-d6) delta: 7.01 (1H, d, J=2.4 Hz), 8.01 (d, 1H, J=3.4 Hz).

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; Berthel, Steven Joseph; Kester, Robert Francis; Murphy, Douglas Eric; Prins, Thomas Jay; Ruebsam, Frank; Sarabu, Ramakanth; Tran, Chinh Viet; Vourloumis, Dionisios; US2008/21032; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 175277-11-9,Some common heterocyclic compound, 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, molecular formula is C9H14N2O2, 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.

46) 3-(tert-butyl)-N-(6-fluoro-2,3-dimethoxybenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (250 mg, 1.36 mmol, 1.0 eq) in toluene (15 mL) was added 2,4-dimethoxybenzyl amine (227 mg, 1.36 mmol, 1.0 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (15 mL) and then NaBH4 (103 mg, 2.72 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (0.45 mmol, 1.1 eq) in DMF (5 mL) were added the acid (75 mg, 0.407 mmol, 1.0 eq), DIEA (262 mg, 2.04 mmol, 5 eq) and HBTU (205 mg, 0.54 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (20 mL) and washed with 10% aq HCl (1*20 mL), sat NaHCO3 (1*20 mL) and water (4*20 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product. Mass Spectrum (LCMS, ESI Pos.) Calcd. For C18H25FN3O3: 350.0 (M+H), Found 350.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, its application will become more common.

Reference:
Patent; Prosetta Antiviral ,Inc.; Selvarajah, Suganya; Paulvannan, Kumar; (58 pag.)US2018/118679; (2018); 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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C4H3N3O4

Synthesis of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester A 20 L reaction vessel equipped with a digital thermometer and stirrer was charged with 4-nitro-1H-pyrazole-3-carboxylic acid (1.117 Kg, 7.11 mol, 1 wt) and methanol (8.950 L, 8 vol). The reaction mixture was stirred under nitrogen, cooled to 0 to 5 C., thionyl chloride (0.581 L, 8.0 mol, 0.52 vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 22 C. overnight after which time 1H NMR analysis (d6-DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 45 C., the residue treated with toluene and re-concentrated (3*2.250 L, 3*2 vol) under reduced pressure at 40 to 45 C. to give 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210 Kg, 99.5% th).

The synthetic route of 5334-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/55094; (2010); 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. 49633-25-2, name is 3-Isopropylpyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C6H10N2

Part A – 4-Bromo-3-isopropylpyrazole To a stirred solution of sodium acetate (19.7 g., 0.24 mole) in acetic acid (100 ml.) and water (15 ml.), 3-isopropylpyrazole (11.0 g., 0.1 mole) was added, followed by dropwise addition of bromine (16.0 g., 0.11 mole) keeping the internal temperature below 15 C. The mixture was kept at 25 C. for 15 hours, treated with water (200 ml.) and extracted with ethyl ether (3 * 50 ml.), and the ether layer washed with water (1 * 50 ml.) dried, (sodium sulfate) and evaporated under reduced pressure. The resultant pale yellow oil was distilled to give 4-bromo-3-isopropylpyrazole (15.3 g., 81%) with a boiling point of 85 C. at 0.06 mm Hg. Analysis: Calc’d. for C6 H9 BrN2: C, 38.11; H, 4.80; N, 14.82; Br, 42.27. Found: C, 37.91; H, 4.89; N, 14.83; Br, 42.15.

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; The Upjohn Company; US3957480; (1976); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1280210-79-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1280210-79-8 name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of tert-butyl 4,6-dihydropyrrolo[3,4- c]pyrazole-5(2H)-carboxylate (15.0 g, 71.8 mmol) in DMF (150 mL) was added NaH (60% in mineral oil) (8.6 g, 215.4 mmol) while the reaction mixture was cooled with an ice bath. When the addition was complete, the resulting mixture was allowed to warm to room temperature and was stirred at room temperature for 30 min. At this point, l-bromo-2- methoxyethane (19.8 g, 143.6 mmol) was added into the reaction mixture, and stirring was continued at room temperature for 2 h. The reaction mixture was then quenched with water (300 mL), and extracted with EtOAc (150 mL x 3). The combined organic layer was washed with brine (100 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 30 : 1) to give a mixture of 122 and 122-A (19.0 g, 99%) as a colorless oil. MS 268.2 [M + H]+. [0072] Synthesis of 123 and 123-A. To a solution of 122 and 122-A (6.5 g, 24.3 mmol) in DCM (60 mL) cooled with an ice bath was added TFA (30 mL). The reaction mixture was stirred at room temperature for 1 h, whereupon the solvent was removed in vacuo to give 123 and 123-A as a crude product mixture which was used directly in the next step without further purification. MS 168.1 [M+H]+. (0114) [0073] Synthesis of 124 and 124-A. To a solution of 123 and 123-A (24.3 mmol, crude product from last step) and A4 (9.3 g, 20.3 mmol) in DMSO (200 mL) was added Na2C03 (21.5 g, 203 mmol), and the reaction mixture was stirred at room temperature for 4 h. The mixture was then diluted with water (400 mL) and extracted with EtOAc (200 mL x 3). The combined organic layers were washed with brine (100 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 30 : 1) to give a mixture of 124 and 124-A (4.5 g, 50%) as a yellow solid. MS 411.0, 413.1 [M+H]+. Example 8. Synthesis of Compound 8 (0126) (0127) [0081] Synthesis of 129 and 129-A. A mixture of 124 and 124-A (350 mg, 0.85 mmol), 2-fluorophenylboronic acid (143 mg, 1.02 mmol) and K2CO3 (352 mg, 2.55 mmol) in dioxane/H20 (10 mL/2 mL) was treated with Pd(PPh3)4 (49 mg, 0.04 mmol) under a N2 atmosphere. The reaction mixture was stirred at 90 C for 3 h and then concentrated in vacuo. The crude residue was taken up in EtOAc (30 niL), and the resulting solution was washed with brine (10 mL x 3). The organic layer was dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by Prep-TLC (PE : EA = 5: 1) to give a mixture of 129 and 129-A (300 mg, 83%) as a yellow solid. MS 427.2 [M + H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; RODIN THERAPEUTICS, INC; FULLER, Nathan, Oliver; LOWE, John, A.; (45 pag.)WO2019/32528; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 52222-73-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 52222-73-8 name is 4-(Trifluoromethyl)-1H-pyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(5)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(4-(trifluoromethyl)- lH-pyrazol- l-vDpropanamide C16H12F6N (0773) (0774) [00351] To a solution of 4-trifluoromethyl-pyrazole (0.20 g, 0.00147 mol) in anhydrous THF (10 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.18 g, 0.004409 mol). After addition, the resulting mixture was stirred for 3 h. (7?)- 3-Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (8) (0.516 g, 0.00147 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using DCM and ethyl acetate (19: 1) as eluent to afford 0.30 g (50%) of the titled compound as white foam. (0775) [00352] Compound 1017 was characterized as follows: NMR (400 MHz, DMSO-i delta 10.38 (s, 1H, NH), 8.45 (d, = 2.0 Hz, 1H, ArH), 8.25-8.22 (m, 2H, ArH & Pyrazole-H), 8.11 (d, = 8.2 Hz, 1H, ArH), 7.82 (s, 1H, Pyrazole-H), 6.39 (s, 1H, OH), 4.55 (d, = 14.0 Hz, 1H, CH), 4.37 (d, = 14.0 Hz, 1H, CH), 1.40 (s, 3H, CH3); Mass (ESI, Positive): 407.0945 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethyl)-1H-pyrazole, and friends who are interested can also refer to it.

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