Day: June 25, 2021

Some common heterocyclic compound, 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, molecular formula is C4H5N3O2, 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: C4H5N3O2

General procedure: Compound 30-3 and 3-bromo-2-(bromomethyl)prop-l -ene are combined with K -CO . in DMF to give compound 47-1. Compound 47-1 is combined with lithium bis(trimethylsilyl)amide to give compound 47-2, Compound 47-2 is combined with NaB in MeOH to give compound 47-3, Compound 47-3 is combined with compound 1-1, PPh3, and DIAD in THF to give compound 47-4. To compound 47- 4 in MeOH is added Pd/C, and the mixture is stirred under H2 to produce compound 47-5. Compound 47- 5, compound 5-5, and TsOH are combined in 1 ,4-dioxane to give compound D-52

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5334-39-4, its application will become more common.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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. category: pyrazoles-derivatives

Into a 25 mL round-bottom flask, were placed intermediate 44.3 (300 mg, 0.74 mmol, 1.00 equiv), 1-methyl-1H-pyrazol-4-amine hydrochloride (119 mg, 0.89 mmol, 1.20 equiv), hydrogen chloride in dioxane (0.5 mL) and n-BuOH (5 mL). The reaction was stirred for 12 h at 110 C. Upon completion of the reaction resulting mixture was concentrated under vacuum. The solution was adjusted to pH 9-10 with sodium hydroxide (2M) and resulting solids were collected by filtration. The crude product was purified by recrystallization from methanol to furnish 208.8 mg (61%) of compound 1-45 as a yellow solid. LCMS (ES, mlz): 465.4[M+H] ?H NMR (300MHz, CD3OD): 7.86 (1H, s), 7.54 (1H, s), 6.75-7.11 (1H, t), 4.05 (1H, s), 3.85 (3H, s), 3.78 (4H, t), 2.60 (4H, s), 2.08-2.32 (5H, m), 1.29-1.47 (4H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 127107-23-7, its application will become more common.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); 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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 1H-Pyrazole-4-carbonitrile

General procedure: The appropriate carboxylic acid (1.0 equiv) was treated with oxalylchloride (1.1 equiv) in CH2Cl2 (0.5 M) at 0 C. The reaction mixture wasstirred at room temperature for 1 h. The solvent was removed under N2and the acid chloride (1 equiv) was dissolved in anhydrous CH2Cl2(0.5 M). The appropriate pyrazole (1.0 equiv) was dissolved in CH2Cl2(0.5 M) and cooled to 0 C. The acid chloride (1 equiv) in CH2Cl2 (0.5 M) was added dropwise and the reaction mixture was stirred atroom temperature for 3 h. The mixture was diluted with EtOAc, washedwith saturated aqueous NaCl, and dried over Na2SO4. Evaporationunder reduced pressure yielded the crude product that was purified byflash chromatography (SiO2).

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 31108-57-3.

Reference:
Article; Otrubova, Katerina; Chatterjee, Shreyosree; Ghimire, Srijana; Cravatt, Benjamin F.; Boger, Dale L.; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1693 – 1703;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

51105-90-9, name is Methyl 1H-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. SDS of cas: 51105-90-9

. A solution of methyl 1H-pyrazole-4-carboxylate (500 mg, 3.97 mmol) and dry THF (10 mL) was added to a 0 C (ice/water) suspension of sodium hydride in mineral oil (317 mg, 60% purity,7.93 mmol) and dry THF (10 mL) and was stirred for 1 h with gradual warming to 10 C. The reaction was then treated with a solution of SEM-Cl (793 mg, 4.76 mmol) and dry THF (5 mL) at 0 C and was stirred overnight at 10 C. The reaction was quenched with saturated aqueous NH4C1 (20 mL) and concentrated to dryness. The aqueous phase was extracted with ethyl acetate (20 mL x 2), dried over anhydrous Na2504, filtered, and concentrated to dryness. Theresidue was purified by flash column chromatography (gradient eluent: petroleum ether: ethyl acetate = 100:0 to 85:15) to provide the title compound (400 mg, 39% yield) as a colorless oil. MS (ESI): mass calcd. for C11H20N2O3Si, 256.12; m/z found, 256.9 [M+H]t ?HNMR (400IVIHz, CDC13): oe 8.06 (s, 1H), 7.94 (s, 1H), 5.43 (s, 2H), 3.84 (s, 3H), 3.57 (t, J 8.0 Hz, 2H), 0.91 (t, J= 8.0 Hz, 2H), -0.02 (s, 9H).

The synthetic route of 51105-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BACANI, Genesis M.; CHAI, Wenying; KOUDRIAKOVA, Tatiana; KRAWCZUK, Paul J.; KREUTTER, Kevin D.; LEONARD, Kristi; RIZZOLIO, Michele C.; SEIERSTAD, Mark; SMITH, Russel C.; TICHENOR, Mark S.; VENABLE, Jennifer D.; WANG, Aihua; (452 pag.)WO2018/112382; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1453-58-3, These common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, 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-Methyl-1H-pyrazole (1 g, 12.18 mmol), phenylboronic acid (3 g, 24.36 mmol) and pyridine (2 mL, 24.36 mmol) were dissolved (160 mL) and Cu(AcO)2 (3.32 g, 18.27 mmol) and molecular sieves were added and mixture was stirred at r.t. for 48 h. Suspension was filtered through Celite and concentrated and the crude thus obtained was purified by normal phase chromatography using hexane/ethyl acetate from 0% to 7.5% to yield the title compound (83% yield). LRMS: m/z 159 (M+1)+ Retention time: 2.83 min (Method B) 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.38 (s, 3 H) 6.25 (d, J=2.34 Hz, 1 H) 7.18-7.32 (m, 1 H) 7.42 (t, 2 H) 7.65 (dd, J=8.60, 1.17 Hz, 2 H) 7.81 (d, J=2.34 Hz, 1 H).

Statistics shows that 3-Methylpyrazole is playing an increasingly important role. we look forward to future research findings about 1453-58-3.

Reference:
Patent; Almirall, S.A.; Erra Sola, Montserrat; Aguilar Izquierdo, Nuria; Carrascal Riera, Marta; Taboada Martinez, Lorena; Navarro Romero, Eloisa; Vidal Juan, Bernat; EP2390252; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 2033-45-6, 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. 2033-45-6, name is 3,5-Dimethyl-4-iodopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 79 (3OOg, 135 immol) in 100 mL of degassed TI-IF was added successively Cul(257mg, i.35mmoi), 2 (2.65g, 27O2mmoi), Pd(PPh3)2C12 (948mg, i.35mmol) and Et3N (410g.40.54rnmol). The mixture was stirred at 80 C for 18 hours. LCM showed that the reaction was completed. The reaction mixture was filtered and the filtrate was concentrated and purified by chrornatograph column to give the product 80 (2.2 g, yield 85%).LCMS: in/z 193 (M+H)t

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, 3,5-Dimethyl-4-iodopyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 92525-10-5, 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. 92525-10-5 name is 3-Iodo-1-methyl-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.

A suspension of 3 ,3-dimethyl-6- (4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)indolin-2-one (200 mg) and 5-bromo-2-methylpyrimidine (181 mg) in 1,4-dioxane (2 ml) and aqueous sodiumcarbonate (2 M) was flushed with argon, then [1,1?-bis(diphenylphosphino)ferrocene] dichloropalladium(II) (26 mg) was added and stirring was continued at 115 C for 3 h. The mixture was evaporated and the residue purified by flash chromatography (silica gel, gradient, 0% to 10% MeOH in dichloromethane) to give the title compound (148 mg, 84%) as a brown solid. MS (mlz): 254.2 [(M+H) :_The title compound was prepared in analogy to example ic using 3,3-dimethyl-6-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)indolin-2-one from example lb and 3-iodo- i-methyl-i Hpyrazole to give the title compound (26%) as an off-white solid. MS (mlz): 242.1 [(M+H)?i.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodo-1-methyl-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 162758-35-2, name is 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid, molecular formula is C17H11Cl3N2O2, 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: C17H11Cl3N2O2

3.8 ml dichlorosulfoxide was added to a suspension of 6.7g of the intermediate (4) in 70 ml toluene, the mixture was refluxed for 3 hours, evaporated in vacuum to dryness. The residue was dissolved in 70 ml toluene, and evaporated in vacuum to dryness, such evaporation was repeated for three times to give 6.2 g of yellow solid intermediate (5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 162758-35-2, its application will become more common.

Reference:
Patent; Beijing Molecule Science and Technology Co., Ltd.; EP1975168; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 37622-90-5, 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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Step A: tert-Butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (3.62 g, 13.0 mmol) was combined with ethyl 4-pyrazolecarboxylate (2.0 g, 14 mmol) in 50 mL of DMF. The mixture was cooled to 0 C., and sodium hydride (467 mg, 19.5 mmol) was added. The reaction mixture was then heated at 50 C. for 10 h. Afterwards, it was diluted with diethyl ether (100 ml), washed with water (5×100 mL) and brine (1×10 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by MPLC (silica gel, 5-100% EtOAc/hexanes) afforded the desired product. ESI-MS calculated for C16H25O4: 323.39. found 346 (M+Na).

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-pyrazolecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Goble, Stephen D.; Mills, Sander G.; Yang, Lihu; Pasternak, Alexander; US2007/238723; (2007); A1;,
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. 637336-53-9, name is Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate

Synthesis of Compound 37.4 [0328] To a solution of 37.3 (200 mg, 0.51 mmol, 1.0 eq) in DCM (10 mL) were added methyl 4-amino-l-methyl-lH-pyrazole-3-carboxylate (80 mg, 0.51 mmol, 1.0 eq), HATU (194 mg, 0.51 mmol, 1.0 eq) and DIPEA (130 mg, 1.02 mmol, 2.0 eq). After stirred at room temperature for 12 h, the reaction mixture was washed with water (10 mL), brine (10 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-TLC (DCM / MeOH = 30 / 1) to give 37.4 (320 mg, yield: 85%) as a white solid. 1H NMR (400 MHz, DMSO- 6) D delta: 10.27 (s, 1H), 9.07 (s, 1H), 8.42 (s, 1H), 8.39 (d, J = 5.6 Hz, 1H), 7.51 (d, J = 5.6 Hz, 1H), 7.27 (s, 1H), 6.81 (t, J =5.6 Hz, 1H), 4.31 (t, J = 6.4 Hz, 2H), 3.95 (s, 3H), 3.93 (s, 3H), 2.95-2.91 (m, 2H), 1.77-1.71 (m, 2H), 1.43-1.36 (m, 4H), 1.36 (s, 9H); ESI-MS (M+H) +: 529.2.

The synthetic route of 637336-53-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC.; JENKINS, Tracy; VESSELS, Jeffery; WO2014/143672; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics