Day: June 17, 2021

Related Products of 15115-52-3, These common heterocyclic compound, 15115-52-3, name is 4-Bromo-1-phenyl-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.

Intermediate I-1 (15 mg, 0.045 mmol) and 4-bromo-1-phenyl-1H-pyrazole (14.93 mg, 0.067 mmol) were dissolved in DMF (446 muL). PdCl2(dppf)-CH2Cl2 (2.187 mg, 2.68 mumol) was added and the reaction mixture was degassed by bubbling with argon for 15 minutes. Sodium carbonate (2 M, 26.8 muL, 0.054 mmol) was added and the reaction mixture was degassed for 5 minutes, then sealed and heated to 90 C in the microwave for 30 minutes. The reaction mixture was diluted with DMF, filtered, and purified by preparative HPLC (Method D, 40 to 75% B in 20 minutes) to give Example 2 (3.0 mg, 0.00823 mmol, 18.4%): 1H NMR (500MHz, METHANOL-d4) delta 8.89 (s, 1H), 8.61 (s, 1H), 8.34 (s, 1H), 7.86-7.75 (m, 3H), 7.70-7.56 (m, 2H), 7.55-7.48 (m, 2H), 7.40-7.33 (m, 1H), 2.62 (s, 3H); LC-MS: Method H, RT = 1.18 min, MS (ESI) m/z: 352.9 (M+H)+ Analytical HPLC Method B: 96.6% purity.

The synthetic route of 15115-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy M.; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; (111 pag.)WO2018/13772; (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. 400877-57-8, name is Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate

A solution of l-methyl-4-nitro-lH-pyrazole-3-carboxylic acid methyl ester (4.8 g, 25.94 mmol) in dry MeOH (100ml) was thoroughly purged with argon, treated with 10% Pd-C (2.7 g, 2.59 mmol), and again purged with argon. Then the reaction mixture was hydrogenated under a balloon pressure of hydrogen at rt for overnight. The reaction mixture was filtered through a bed of celite. The filtrate was concentrated and dried to give the title compound as gray-white solid (3.4 g, 84%), which was used in the next reaction step without further purification.

The synthetic route of 400877-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLEICHER, Konrad; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; GRUBER, Felix; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RODRIGUEZ SARMIENTO, Rosa Maria; WO2011/154327; (2011); 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. 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide

General procedure: To a solution of aromatic aldehydes 8 (1.0 mmol) in acetonitrile, 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 10 (1.0 mmol) and InCl3 (10 mol%) were added at room temparature and the reaction mixture was stirred till the completion of the starting materials (indicated by TLC). The solvent was evoparated and the crude product was triturated with 10% diethyl ether in hexane to obtain the pure product. The product was identified by 1H NMR, 13 C NMR and Mass.

The synthetic route of 139756-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mulakayala, Naveen; Kandagatla, Bhaskar; Ismail; Rapolu, Rajesh Kumar; Rao, Pallavi; Mulakayala, Chaitanya; Kumar, Chitta Suresh; Iqbal, Javed; Oruganti, Srinivas; Bioorganic and Medicinal Chemistry Letters; vol. 22; 15; (2012); p. 5063 – 5066;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1029413-51-1,Some common heterocyclic compound, 1029413-51-1, name is 4-Amino-1-(1-boc-azetidin-3-yl)-1H-pyrazole, molecular formula is C11H18N4O2, 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.

[0483j To a solution of N-(2-(2-chloropyrimidin-4-yl)-6,7,8 ,9-tetrahydro-5H- benzo [7] annulen-5 -yl)-3 -isopropoxyazetidine- 1 -carboxamide (130 mg, 0.32 mmol) in 1,4- dioxane (5 mL) were added 1-ethyl-1H-pyrazol-4-amine (36 mg, 0.32 mmol), Pd2(dba)3 (29 mg, 0.032 mmol), S-Phos (26 mg, 0.064 mmol) and Cs2CO3 (312 mg, 0.96 mmol). The mixture was stirred at 100 C for 2 h. After diluted with water (50 mL), the mixture was extracted with EtOAc (60 mL x 2). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by prep-HPLC (CH3CN/H20 with 0.05% NH4OH as mobile phase) to give N-(2-(2-(( 1-ethyl-i H-pyrazol-4-yl)amino)pyrimidin-4-yl)-6,7,8 ,9-tetrahydro-5H- benzo[7]annulen-5-yl)-3-isopropoxyazetidine-1-carboxamide as a yellow solid (129 mg, yield:73%). [0574j Synthesis of tert-butyl 3 -(4-((4-(4-((3 -(tert-butoxy)azetidine- 1- carboxamido)methyl)-3 -(trifluoromethyl)phenyl)pyrimidin-2-yl)amino)- 1H-pyrazol- 1- yl)azetidine-1-carboxylate was similar to that of Example 161. The residue was purified by silica gel chromatography column (EtOAc: petroleum ether = 10:1) to give tert-butyl 3-(4-((4-(4- ((3 -(tert-butoxy)azetidine- 1 -carboxamido)methyl)-3 -(trifluoromethyl)phenyl)pyrimidin-2- yl)amino)-1H-pyrazol-1-yl)azetidine-1-carboxylate as a yellow solid (230 mg, yield: 46%). ESIMS (M+H) : 645.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-1-(1-boc-azetidin-3-yl)-1H-pyrazole, its application will become more common.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 112758-40-4,Some common heterocyclic compound, 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

Preparation of 1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde; Intermediate 1 To a solution of ethyl 3-methyl-1H-pyrazole-4-carbaldehyde (6.4 g, 58.0 mmol) in 60 mL of anhydrous N,N-dimethylformamide were added potassium carbonate (10.8 g, 77.8 mmol) and 2,4-dichloropyrimidine (8.64 g, 58.0 mmol) at room temperature. The resulting suspension was stirred for 14 hours at room temperature with monitoring a reaction with LC-MS or thin layer chromatography (TLC). The reaction mixture was diluted with ethyl acetate and washed with brine (*2). The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by silica gel chromatography using a mixture of heptanes and ethyl acetate to afford the desired intermediate 1 as a white solid (5.47 g, 42%); MS (ESI) m/z 223 [M+H]+, 1H NMR (300 MHz, CDCl3) delta 10.06 (s, 1H), 9.04 (s, 1H), 8.70 (d, 1H, J=5.4 Hz), 7.87 (1H, d, J=5.4 Hz), 2.59 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyl-1H-pyrazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Lee, Jaekyoo; Choi, Jang-Sik; Hwang, Hae-Jun; Song, Ho-Juhn; Kim, Jung-Ho; Kim, Se-Won; Koh, Jong Sung; Lee, Jaesang; Lee, Tae-Im; Choi, Yung-Geun; Park, Sung-Ho; Lee, In Yong; Suh, Byung-Chul; Salgaonkar, Paresh Devidas; Jung, Dong-Sik; US2015/111883; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 28466-26-4, These common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, 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.

Acetic anhydride (0.7 ml, 8.433 mmol) was added dropwise at 0 C. to 1H-pyrazol-4-amine (0.7 g, 8.433 mmol). The mixture was stirred for 30 min at RT and quenched by the addition of crushed ice. The mixture was extracted with ethyl acetate The combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the product in 54% yield. (0.6 g). LC-MS (ESI): Calculated mass: 125.0; Observed mass 126.0 [M+H]+ (rt: 0.115 min).

Statistics shows that 4-Aminopyrazole is playing an increasingly important role. we look forward to future research findings about 28466-26-4.

Reference:
Patent; Linnanen, Tero; Wohlfahrt, Gerd; Nanduri, Srinivas; Ujjinamatada, Ravi; Rajagopalan, Srinivasan; Mukherjee, Subhendu; US2015/11548; (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. 27006-76-4, name is 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H7ClN2O

General procedure: Toa stirred solution of substituted phenol (75 mmol) in DMF or DMSO (25mL), wasadded solid potassium hydroxide (90 mmol) at room temperature. The resultingmixture was stirred at 45 Cfor 2 h and then 5-chloropyrazole-4-carbaldehyde (5) (50 mmol) was added in portions. The reaction mixture was heatedto 110C. After6-22 h, the mixture was poured into water and extracted with ethyl acetate. Thecombined extracts were dried over anhydrous magnesium sulfate, filtered, andconcentrated to obtain compounds 6a-6z. Then the product 6 (10mmol) was added into a stirred mixture of hydroxylamine hydrochloride(15 mmol) and potassium hydroxide (20 mmol) in methanol or ethanol (30 mL) atthe room temperature. The reaction mixture was refluxed for 5-20 h. Oncompletion, the mixture was poured into water (80 mL), and the solidprecipitate was filtered, washed with water, and dried to afford thecorresponding pyrazole oximes 7a-7z, which were used for the following transformations withoutfurther purification.

The synthetic route of 27006-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dai, Hong; Li, Gang; Chen, Jia; Shi, Yujun; Ge, Shushan; Fan, Chongguang; He, Haibing; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3818 – 3821;,
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. 13808-62-3, name is 4-Methyl-3-phenyl-1H-pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C10H10N2

General procedure: A mixture of (E)-2-methyl-3-phenylacrylaldehyde (1c) (146 mg, 1.0 mmol) and TsNHNH2 (205 mg, 1.1 mmol) in CH3CN (2 mL) were stirred at room temperature for 3 h and then CH3CN (2 mL), NaOH (44 mg, 1.1 mmol) were added and the mixture was heated at reflux for 15 h, then NaOH (60 mg, 1.5 mmol) and benzyl bromide (255 mg, 1.5 mmol) were subsequently added and the mixture was stirred at room temperature for 2 h. The product was extracted with Et2O and the organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel afforded the desired product 4k as colorless oil (233 mg, 94%).

The synthetic route of 13808-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tang, Meng; Zhang, Fu-Min; Tetrahedron; vol. 69; 5; (2013); p. 1427 – 1433;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 345637-71-0, 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. 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-(5-methyl-3-(trifluoromethyl)-l H-pyrazol- l -yl)acetic acid ( 129 mg, 0.6 mmol) in N, N-dimethyformamide ( 5 mL), l -[bis(dimethylamino)methylene]- l H-l ,2,3-triazolo[4,5-b]pyridinium 3- oxid hexafluorophosphate (HATU) (258 mg, 0.7 mmol) and N, N-diisopropylethylamine (0.6 mL, 3.4 mmol) was added. The resulting clear solution was stirred for 10 min at 25 C. N-((2,6- difluorophenyl)(methyl)(o o)-lambda6-sulfanylidene)-2-(piperidin-4-yl)thiazole-4-cai·boxamide (21 8 mg, 0.6 mmol) was added and the resulting yellow solution was stirred for 16 h at 25 C. After completion of the reaction, the reaction mixture was quenched with a brine solution ( 1 50 mL). The reaction mixture was extracted twice with ethyl acetate (50 mL). The ethyl acetate layer was concentrated and the residue was purified using column chromatography using 80% ethyl acetate in hexane as an eluent to obtain N-((2,6- difluorophenyl)(methyl)(oxo)-6-sulfanylidene)-2-( l -(2-(5-methyl-3-(trifluoromethyl)- l H^yl)acetyl)piperidin-4-yl)thiazole-4-carboxamide (26 mg, 0.05 mmol, 8% yield).-NMR (400 MHz, DMSO-d6) delta 8.28 (s, 1 H), 7.80-7.87 (m, 1 H), 7.38 (t, J = 9.0 Hz, 2H), 7.1 8 (t, J = 53.3 Hz, 1 H), 7.04 (t, J = 54.2 Hz, 1 H), 6.92-7.22 (m, 1 H), 5.40 (dd, J = 33.2, 16.6 Hz, 2H), 4.35 (d, J = 13.0 Hz, 1 H), 3.97 (d, J = 13.0 Hz, 1 H), 3.72 (s, 3H), 3.25 (t, J = 1 1 .9 Hz, 1 H), 2.79-2.85 (m, 1 H), 2.08 (s,3H), 1 .78 (dd, J = 28.0, 1 5.0 Hz, 1 H), 1 .50- 1 .59 (m, 1 H)

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, 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PI INDUSTRIES LTD.; SHANBHAG, Gajanan; SHARMA, Aditya; RENUGADEVI, G.; PABBA, Jagadish; DENGALE, Rohit Arvind; ROY, Dipankar; S.P., Mohan Kumar; BELKAR, Yogesh Kashiram; AUTKAR, Santosh Shridhar; GARG, Ruchi; VENKATESHA, Hagalavadi M; KLAUSENER, Alexander Guenther Maria; (114 pag.)WO2019/48988; (2019); 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. 330792-70-6, name is 3-Amino-5-(4-phenoxyphenyl)pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C16H12N4O

3-Amino-4-cyano-5-(4-phenoxyphenyl)pyrazole (100g) was suspended in formamide (500ml) and heated at a temperature of 135-140°C, after completion of reaction, the reaction mixture was cooled to a temperature of 30-35°C and demineralized water (1000ml) was added and the reaction mixture was stirred at a temperature of 20-25°C for 1 hour. The resulting solid was filtered, washed with water (500ml) then successively slurry washed with toluene (2 x 500ml) and dried to afford pure 4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine compound of formula I (70g) having purity 99.8percent measured by HPLC; assay > 98percent; residue on ignition 0.05percent; heavy metals <20ppm. According to the analysis of related databases, 330792-70-6, the application of this compound in the production field has become more and more popular. Reference:
Patent; IND-SWIFT LABORATORIES LIMITED; ARUL, Ramakrishnan; SARIN, Gurdeep Singh; WAS, Sandeep; KUMAR, Vishal; (26 pag.)WO2017/163257; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics