Day: August 9, 2021

Electric Literature of 852227-86-2, A common heterocyclic compound, 852227-86-2, name is 5-(Chloromethyl)-1,3-dimethyl-1H-pyrazole, molecular formula is C6H9ClN2, 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.

A mixture of 3C (1 g, 3.06 mmol), 5-(chloromethyl)- 1 ,3-dimethyl- 1 H-pyrazole (0.531 g, 3.67 mmol) and cesiumcarbonate (2.99 g, 9.19 mmol) in DMA (12 mL) was stirred at rt for 3 d. The reactionmixture was absorbed onto CELITE and chromatographed on an 80 gm ISCO silica gel cartridge, eluting with a 0-9% MeOH/CH2C12 gradient. The purest fractions wereconcentrated to afford 610 mg of product. The mixed fractions were concentrated to afford 350 mg of material that was triturated with ethyl acetate to afford 155 mg of awhite solid. This was combined with the purest fractions to afford 185A (766 mg, 1.762 mmol, 58% yield) as a yellow solid. ?H NMR (400MHz, DMSO-d6) oe 8.47 (d, J5.1 Hz, 1H), 7.42 (d, J=0.6 Hz, 1H), 7.35 – 7.26 (m, 2H), 5.46 (s, 1H), 5.20 (s, 2H), 3.50 (s, 3H),3.39 (td, J=6.7, 2.5 Hz, 2H), 2.79 (t, J=6.8 Hz, 2H), 2.00 (s, 3H). MS(ESI) m/z 436.3 (M+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; BRISTOL-MYERS SQUIBB COMPANY; HART, Amy C.; PITTS, William J.; MASTALERZ, Harold; GUO, Junqing; BROWN, Gregory D.; (148 pag.)WO2016/100166; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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. HPLC of Formula: C7H13N3

A mixture of 2,4-dichloro-6-methylpyrimidine (3.52g, 22mmol) and 5-amino-3-tert- butyl-lH-pyrazole (3.00g, 22mmol) and anhydrous sodium carbonate (2.29g, 22mmol) in ethanol (75ml) was stirred at ambient temperature for 24 hours. The insoluble material was removed by filtration and the solvent removed from the filtrate by evaporation. The residue EPO was purified by chromatography on silica gel eluting with EtOAc / isohexane (1:3) and then methanol / DCM (5:95) to give 2-chloro-6-methyl-4-(5-tert-butyl-lH-pyrazol-3- ylamino)pyrimidine (3.16g, 55%); NMR Spectrum 1.31 (s, 9Eta), 2.19 (s, 3H), 6.15 (s, IH), 7.25 (s, IH), 10.13 (s, IH), 12.14 (s, IH); Mass Spectrum 266 [MH]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 82560-12-1, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/100461; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 42027-81-6, A common heterocyclic compound, 42027-81-6, name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, molecular formula is C5H7N3O3, 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 stirred solution of 2-(4-nitro-1H-pyrazol-1-yl)ethanol 17 (2.0 g, 1.23 mmol) in EtOH (25 mL), 0.40 g of Pd(OH)2 added and then stirred reaction under H2 gas atm for 1 4h. After the completion of reaction (TLC monitoring) the reaction mixture was filtered through celite bed, washed with MeOH, concentrated the solvent and the crude compound was purified by triturating with ether and pentane to give 2-(4-amino-1H- pyrazol-1-yl)ethanol precursor-07 as brown solid (1.30 g, 81% yield). MS: 128.07 (M+H).

The synthetic route of 42027-81-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; KETHIRI, Raghava Reddy; VISWANADHAN, Vellarkad Narayana; GIRI, Sanjeev; WO2015/25197; (2015); 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., name: 1-Nitropyrazole

Example 5 (S)-3-Cyclopentyl-N-[1-(2-methoxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionamide 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 hexanes (160 mL). A white solid precipitated which was filtered and dried in vacuo, to afford 3-nitro-1H-pyrazole (3.16 g, 79%): 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; Brinkman, John A.; Hayden, Stuart; Haynes, Nancy-Ellen; Kester, Robert Francis; McDermott, Lee Apostle; Qian, Yimin; Sarabu, Ramakanth; Scott, Nathan Robert; Tilley, Jefferson Wright; US2009/264445; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 863548-52-1,Some common heterocyclic compound, 863548-52-1, name is (1-Methyl-1H-pyrazol-5-yl)methanamine, molecular formula is C5H9N3, 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.

1 1 8 Synthesis of Compound 8 (Formula 7^/Example 1; The lithium salt of 3-cyclobutyl-2,3,4,5-tetrahydro-lH-benzo[d]azepine-7-carboxyhc acid (7)( 0.502g, 2mmol) was stirred in thionyl chloride (7.3OmL, lOOmmol) for 60 minutes and then concentrated in vacuo and azeotroped with toluene to give the acid chloride as a brown solid This material was suspended in dichloromethane (1OmL) and to this was added C-(2-methyl-2H-pyrazol-3-yl)-methylamine (0 22g, 2mmol) and triethylamine (0.28mL, 8mmol) and the reaction stirred for 18 hours. The reaction mixture was concentrated in vacuo and loaded onto an SCX-2 cartridge (2Og) eluting firstly with methanol (1OmL x3) and then 2M ammonia/methanol. Fractions corresponding to the product were combined and concentrated in vacuo and then purified by silica chromatography using methanol/dichloromethane mixtures with added ammonia to give 3-cyclobutyl-N-(( 1 -methyl- 1 H-pyrazol-5-yl)methyl)-2,3 ,4,5-tetrahydro- 1 H-benzo[d]azepine-7- carboxamide (8) in 0.9mmol.1H NMR (400 MHz, DMSO-Cl6): delta 8.80 – 8.91 (m, IH), 7.57 – 7.66 (m, 2H), 7.26 – 7.33 (m, IH), 7.16 – 7.23 (m, IH), 6.11 – 6.18 (m, IH), 4.45 – 4.53 (m, 2H), 3.81 (s, 3H), 2.81 – 2.94 (m, 4H), 2.69 – 2.80 (m, IH), 2.34 (br. s., 4H), 1.95 – 2.06 (m, 2H), 1.71 – 1.84 (m, 2H), 1.49 – 1.65 (m, 2H)

The synthetic route of 863548-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED.; POONI, Parminder, Kaur; MERCHANT, Kevin, John; KERR, Catrina; CROSBY, Stuart, Richard; OKAWA, Tomohiro; SASAKI, Mitsuru; GOTOU, Mika; SHOWELL, Graham, Andrew; TEALL, Martin, Richard; WO2010/7382; (2010); 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.

The reaction was carried out on a three times 1 g scale. 2-Chloro-/V- [(dimethylamino)methylidene]-5-[(diphenylmethylidene)amino]pyridine-3-sulfonamide (3.00 g, 7.03 mmol) and 4-(trifluoromethyl)-1 H-pyrazole (1 .43 g, 10.5 mmol) were dissolved in DMSO (1 10 ml, 1 .6 mol) and potassium iodide (583 mg, 3.51 mmol) and potassium phosphate (2.24 g, 10.5 mmol) were added. The reaction was heated for 5h in the microwave at 100C. Afterwards, the solid was filtered off and to the filtrate ethyl acetate and water were added. The organic phase was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the crude was purified by chromatography on silica gel (Biotage, ethyl atecate / hexane) to yield 15.7 g (424 % yield). (0499) LC-MS (Method A): Rt = 1.40 min; MS (ESIpos): m/z = 472 [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; BAYER AKTIENGESELLSCHAFT; HAUFF, Peter; WERNER, Stefan; (94 pag.)WO2019/81573; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 2075-46-9,Some common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

The solution of 4-nitro-1H-pyrazole (SM6, 10 g, 88.44 mmol), NaH(60%, 1.3 eq, 4.60 g, 114.97mmol) and iodomethane (SM7, 25 g, 177 mmol) in Dry DMF (100 ml) was stirred at 0C overnight, and then cooled to room temperature and quenched with water (200 mL) and extracted with EA. The organic layer was dried over anhydrous Na2SO4 to obtain the target compound 12(11 g, 92 % yield).

The synthetic route of 2075-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hangzhou Rex Pharmaceutical Co., Ltd; WANG, Yonghui; ZHOU, Juan; GAO, Yujun; WANG, Dong; HONG, Binbin; SHEN, Ximing; WU, Yaodong; LI, Chunqi; EP3476848; (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, Safety of 4-Iodo-1-methyl-1H-pyrazole

tert-butyl 3 ,8-diazabicyclo [3.2.1 ]octane-3-carboxylate (250 mg, 1.18 mmol), 4-iodo- 1-methyl- 1H-pyrazole (0.32 g, 1.5 mmol), sodium 2-methylpropan-2-olate (0.17 g, 1.8 mmol), methanesulfonato(2-dicyclohexylphosphino-2?,6?-di-i-propoxy- 1,1 ?-biphenyl)(2?-amino- 1,1biphenyl-2-yl)palladium(II) (0.10 g, 0.12 mmol) and toluene (4 mL) were charged in a vial. The headspace was flushed with nitrogen and the reaction mixture was degassed using 4 cycles of vacuum and nitrogen refilling. The reaction was heated at 110 C for 24 h then cooled to room temperature. Silica gel was added and the solvent was removed under vacuum. The desired product was purified by silica gel chromatography (eluting with hexanes/ ethyl acetate methanol). The title compound was obtained as a solid (350 rng). LCMS M/Z (M+H) 293.

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

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; COTE, Alexandre; CRAWFORD, Terry; DUPLESSIS, Martin; GOOD, Andrew, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; (271 pag.)WO2016/138114; (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 155377-19-8 as follows. Formula: C7H7F3N2O2

A. N-(ADAMANTAN- 1 -YLMETHYL)- 1 -(4-AMINO-5-FLUOROPYRIMIDIN-2-YL)-3 – (TRIFLUOROMETHYL)- lH-PYRAZOLE-4-CARBOXAMIDE (COMPOUND 1); Step 1. Trifluoromethyl-lH-pyrazole-4-carboxylic acid; NaOH (3 mL, 10 N) is added to a solution of 3-trifluoromethyl-lH-pyrazole-4- carboxylic acid ethyl ester (5.0 g, 24 mmol) in MeOH (25 mL) at RT. The mixture is heated to 40 C for 3 h. The solvent is removed to dryness. H2O is added. The solution is acidified with 2N HCl to pH = 6 to afford the title compound as an off-white solid.

According to the analysis of related databases, 155377-19-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROGEN CORPORATION; WO2009/12482; (2009); A2;,
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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Nitro-1H-pyrazole-3-carboxylic acid

Thionyl chloride (6.28ml_, 86.07mmol) was added to an ice cooled solution of 4-nitro-1 H- pyrazole-3-carboxylic acid (10.4 g, 66.21 mmol) in methanol (150 ml_). The resulting solution was stirred at RT ON. The day after MeOH was removed under vacuum; toluene was added and dried again. The solid was suspended in pentane and filtered under vacuum to afford methyl 4-nitro-1 H-pyrazole-3-carboxylate (p68, 1 1.15 g, y= 98%) as creamy solid. MS (mlz): 171 .9 [MH]+

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

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; CREMONESI, Susanna; SEMERARO, Teresa; TARSI, Luca; GIBSON, Karl Richard; (116 pag.)WO2019/81939; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics