Tag: M.W=0-100

Application of 31230-17-8,Some common heterocyclic compound, 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

Compound 2a (3.32 g, 20 mmol), 3-amino-5-meth- ylpyrazole (1.94 g, 20 mmol) and diisopropylethylamine (5.17 g 40 mmol) were added to a solution of2O mE of ethanol and then stirred at room temperature for 2 days. The insoluble substance was collected to obtain Compound 2b (3.9 g. Yield86percent), MS [M+1] 228.0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-pyrazol-3-amine, its application will become more common.

Reference:
Patent; ZHEJIANG HISUN PHARMACEUTICAL CO., LTD.; Ding, Yili; Yang, Xuan; Yan, Qingyan; Bai, Hua; Cai, Lifeng; Smith, Kenneth; Chai, Jian; US2014/378488; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 694-48-4, These common heterocyclic compound, 694-48-4, name is 1,3-Dimethyl-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.

Put 100g (1.04mol, 1eq) of 1,3-dimethylpyrazole into the reaction bottleAnd 800mL water and 400mL ethanol,Add in batches with stirring at room temperature132.1g (0.52mol, 0.5eq) of iodine,Subsequently, 84.8 g (0.624 mol, 0.6 eq) of 25% hydrogen peroxide was added dropwise at 15-20C.Stir at room temperature for 20 hours,Sampling GC to check the remaining material is less than 1%, add 200mL of saturated sodium bisulfite,Distilling ethanol under reduced pressure, cooling to 0, filteringget210.1g of 4-iodine-1,3-dimethyl-1H-pyrazole, GC purity 98.6%,The yield was 91%.

Statistics shows that 1,3-Dimethyl-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 694-48-4.

Reference:
Patent; Xuzhou Shengyuan Chemical Co., Ltd.; Chen Hong; Yu Wanli; (8 pag.)CN111233768; (2020); A;,
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. 930-36-9, name is 1-Methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H6N2

A solution of N-methylpyrazole (5.12 g, 62.4 mmol) in THF (100 mL) was cooled to -78 C. and 2.5 M n-butyllithium in hexane (27.5 mL, 68.8 mmol) was added. After stirring for 30 minutes at the same temperature, 0.5 M zinc chloride in THF (107 mL, 53.5 mmol) and 1 M zinc chloride in diethyl ether (15.3 mL, 15.2 mmol) were added. The mixture was allowed to warm to room temperature and 2-iodo-4-nitroanisole (17.4 g, 62.4 mmol) followed by tetrakis(triphenylphosphine)palladium (3.6 g, 3.1 mmol) were added. After stirring at 60 C. for 20 hours, the black solution was concentrated on a rotary evaporator, and extracted with ethyl acetate and brine. Combined organic layers were dried over magnesium sulfate, filtered, and partly concentrated until a solid started to precipitate. Hexane was added, precipitate was filtered off, and washed with a cold 3:1 mixture of hexane/ethyl acetate to give 5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole (8.6 g, 36.9 mmol, 59%) as a tan solid. LCMS m/z (%/o)=234 (M+H, 100). 1H NMR (400 MHz, CDCl3) delta: 8.34 (dd, J=2.8, 9.2 Hz, 1H), 8.19 (d, J=2.8 Hz, 1H), 7.56 ( d, J=2.0 Hz, 1H), 7.08 (d, J=9.2 Hz, 1H), 6.31 (d, J=1.6 Hz, 1H), 3.96 (s, 3H), 3.74 (s, 3H).

According to the analysis of related databases, 930-36-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Teegarden, Bradley; Xiong, Yifeng; Strah-Pleynet, Sonja; Jayakumar, Honnappa; Dosa, Peter I.; Feichtinger, Konrad; Casper, Martin; Lehmann, Juerg; Jones, Robert M.; Unett, David J.; Karoline Choi, Jin Sun; US2007/207994; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 35277-02-2, The chemical industry reduces the impact on the environment during synthesis 35277-02-2, name is 4-Fluoro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Sodium hydride (60 wt.%, 276 mg, 6.90 mmol) was added to a mixture of 1- (5-chloropyrazin-2-yl)ethanone (800 mg, 5.11 mmol) and 4-Fluoro-1H-pyrazole (484 mg, 5.62 mmol) in N,N-dimethylformamide (6.0 mL) at ambient temperature for 10 minutes. The reaction mixture was then poured into water (70 mL) and was sonicated and stirred for 20 minutes. A dark red solid was isolated by filtration, washed with small amounts of water, and dried to 1 -(5 -(4-fluoro- 1 H-pyrazol- 1 -yl)pyrazin-2-yl)ethan- 1-one (919 mg, 95% yield). MS: M+1 = 207.

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

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; DIPIETRO, Lucian, V.; (105 pag.)WO2018/22761; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 35344-95-7, 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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

2-bromoethoxy- xit y Id i met y I si I ane (CAS [86864-60-0]) (2.4 mL; 1 1 .4 mmol ) was added to a solution of 1 H-pyrazo le-4-carbaldehyde (CAS [35344-95-7] ) (910 mg; 9.5 mmol ) and K2CO3 ( 1 .6 g; 1 1 .4 mmol) in ACN (18 mL ). The reaction was heated at 80C for 2h. The reaction mixture was partitioned between a saturated solution of NaHCO; and EtOAc. The organic layer was separated, dried over MgS04, filtered and evaporated till dryness. The residue was purified by chromatography ov er silica gel ( Stationary phase: irregular SiOH 40 iim 120g, mobile phase gradient from: 100% DCM, 0% MeOH to 95% DCM, 5% MeOH). The fractions containing product were collected and ev aporated to dryness yielding 1 .6 g (65%) of intermediate 12 .

The chemical industry reduces the impact on the environment during synthesis 1H-Pyrazole-4-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PATRICK, Aaron Nathaniel; (161 pag.)WO2018/50684; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1904-31-0,Some common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

Example 113; 4-(3,5-Difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide; To a mixture of 4-(3,5-difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (113b) (0.308 g, 0.00096 mol), EDCI (0.28 g, 0.0015 mol), HOBt (0.21 g, 0.0015 mol) and NMM (0.49 g, 0.0048 mol) in CH2Cl2 (15 mL) was added 1-methyl-1H-pyrazol-3-amine (0.11 g, 0.001 mol) in one portion. The mixture was stirred at room temperature overnight. The reaction mixture was washed with water, aq. citric acid and then sat. NaHCO3. The organic phase was dried over Na2SO4 and concentrated to give a brown oil. The crude oil was purified by prep. HPLC to give the title compound (95 mg, 51percent yield) as a white solid. 1H NMR (400 MHz, CDCl3): delta 8.82 (s, 1H), 7.20 (m, 2H), 7.03 (d, 2H), 6.73 (s, 1H), 6.42 (m, 3H), 3.72 (s, 3H), 2.84 (s, 2H), 1.42 (s, 6H); LCMS for C21H19F2N3O3 m/z 400.4 (M+H)+.

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US2008/280875; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31108-57-3,Some common heterocyclic compound, 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, molecular formula is C4H3N3, 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.

General procedure: The appropriate carboxylic acid (1.0 equiv) was treated with oxalyl chloridie (1.1 equiv) in CH2Cl2 (0.5 M) at 0 C. The reaction mixture was stirred at room temperature for 1 h. The solvent was removed under N2 and the acid chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate pyrazole (1.0 equiv) was dissolved in CH2Cl2 and cooled to 0 C. The acid chloride was added dropwise and the reaction mixture was stirred at room temperature for 3 h. The mixture was diluted withEtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude product that was purified by flash chromatography(SiO2).

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Otrubova, Katerina; Srinivasan, Venkat; Boger, Dale L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3807 – 3813;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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. Formula: C4H6N2

A solution of potassium permanganate (16.17 g, 102.31 mmol) in water (150 mL) was added to a solution of 3-methylpyrazole (4.2 g, 51.15 mmol) in water (100 mL) and the mixture was refluxed overnight. After cooling to room temperature the insoluble material was removed by filtration. The filtrate was concentrated to 30 mL and 2 N HCl was added until a solid was precipitated. The solid was filtered, washed with cold water and dried in vacuo to yield 1H-pyrazole-3-carboxylic acid (3.1 g, 54percent yield) as a white solid which was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1453-58-3, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Trabanco-Suarez, Andres Avelino; Tresadern, Gary John; Delgado-Jimenez, Francisca; US2013/190318; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31108-57-3, These common heterocyclic compound, 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, 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 crude SB (124.8 mg, 0.314 mmol, theoretical amount) in anhydrous THF (3 mL) was added 4-cyanopyrazole (58.5 mg, 0.628 mmol) followed by potassium carbonate (86.8 mg, 0.628 mmol). The solution was heated at 50 C for 2 hours. Then the solution was diluted with ethyl acetate (200 mL). The resulting solution was washed with brine (2×100 mL), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by reverse phase prep-HPLC to afford desired product (34.6 mg, 0.0845 mmol, two steps overall yield=27%) as a white solid. 1HNMR (400 MHz, CDC13) 5(ppm): 7.86 (IH, s), 7.82 (IH, s), 5.01 (IH, AB), 4.91 (IH, AB), 2.61 (IH, t), 2.16-2.26 (2H, m), 2.04 (IH, m), 1.00-1.90 (21H, m), 0.68 (3H, s). LCMS: rt = 2.26 mm, m/z = 410.2 [M+H]+

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGE THERAPEUTICS, INC.; BOTELLA, Gabriel Martinez; HARRISON, Boyd L.; ROBICHAUD, Albert Jean; SALITURO, Francesco G.; BERESIS, Richard Thomas; WO2014/169833; (2014); 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. 36650-74-5, name is 1H-Pyrazole-3-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C4H3N3

To a solution of lH-pyrazole-3-carbonitrile (2.00 g, 21.5 mmol) in EtOH (3 ml) was added ethyl (2R)-oxirane- 2-carboxylate (1.0 g, 8.61 mmol) (for synthesis refer to example 5AY) portionwise. Then the mixture was stirred at 90C for 0.5 h. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by FCC (1 :2 EtOAc / petrol) to give the title compound as a colourless oil. Y = 14 %. NMR (400MHz, chloroform-) delta 7.59 (d, J = 3 Hz, 1H), 6.65 (d, J = 3 Hz, 1H), 4.56 – 4.47 (m, 3H), 4.33 – 4.25 (m, 2H), 1.35 – 1.29 (m, 3H).

The synthetic route of 36650-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NODTHERA LIMITED; BOCK, Mark G.; WATT, Alan Paul; PORTER, Roderick Alan; HARRISON, David; (229 pag.)WO2019/25467; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics