Day: July 13, 2021

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. 1245772-13-7, name is Methyl 1-(2,2,2-trifluoroethyl)-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 1-(2,2,2-trifluoroethyl)-1H-pyrazole-3-carboxylate

Example 256: 2-N-Methyl-2-N-phenyl-6-{5-[1-(2,2,2-trifluoroethyl)-1 H-pyrazol-3-yl]-1 ,2,4- oxadiazol-3-yl}-1 ,3,5-triazine-2,4-diamine (Method 12)Methyl 1-(2,2,2-trifluoroethyl)-1 H-pyrazole-3-carboxylate (Intermediate 204, 0.312 g, 1.5 mmol) was dissolved in a mixture of THF (2 mL), MeOH (2 mL) and water (1 mL); lithium hydroxide (0.188 g, 4.5 mmol) was added and the mixture was stirred at roomtemperature for 16 h. The mixture was concentrated, the residue dissolved in water (1 mL) and the mixture was neutralised. This was extracted with EtOAc (2 x 10 mL), the organic extracts were dried over sodium sulfate and concentrated under vacuum. The crude material was washed with pentane (2 x 10 mL) to afford 1-(2,2,2-trifluoroethyl)-1 H- pyrazole-3-carboxylic acid (0.200 g, 69%). 2-N-methyl-2-N-phenyl-6-{5-[1-(2,2,2- trifluoroethyl)-1 H-pyrazol-3-yl]-1 ,2,4-oxadiazol-3-yl}-1 ,3,5-triazine-2,4-diamine was then prepared from 1-(2,2,2-trifluoroethyl)-1 H-pyrazole-3-carboxylic acid (0.159 g, 0.820 mmol) and 4-amino-N-hydroxy-6-[methyl(phenyl)amino]-1 ,3,5-triazine-2- carboximidamide (prepared in an analogous manner to Intermediate 1 , 0.125 g, 0.483 mmol) according to the method described for Example 251 to afford the title compound (0.110 g, 55%).

The synthetic route of 1245772-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BARKER, Oliver; BENTLEY, Jonathan; BOCK, Mark G.; CAIN, Thomas; CHOVATIA, Praful; DOD, Jennifer Ruth; EUSTACHE, Florence; GLEAVE, Laura; HARGRAVE, Jonathan; HEIFETZ, Alexander; LAW, Richard; RAOOF, Ali; WILLOWS, David; WO2012/35023; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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. Safety of 1-Methyl-1H-pyrazole-5-carboxylic acid

42-1 : 1 -Methyl-N-4-[rel-(4aS,5aS)-5a-methyl-4-oxo-3-(phenylamino)-1 ,4,4a,5,5a,6- hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl-1 H-pyrazole-5-carboxamide A solution of 1 -methyl-1 H-pyrazole-5-carboxylic acid (1 10 mg, 871 muiotaetaomicronIota) and HATU (331 mg, 871 muiotaetaomicronIota) in DMA (3 mL) was added to a mixture of rel-(4aR,5aR)-2-(2-Aminopyridin- 4-yl)-3-anilino-5a-methyl-4a,5,5a,6-tetrahydrocyclopropa[f]indol-4(1 H)-one (26; 100 mg, 290 muiotaetaomicronIota) and DIPEA (152 muIota_, 871 muiotaetaomicronIota) in DMA (3 mL) and stirred for 16 h at 50. The mixture was concentrated, DCM added and washed with water and dried over sodium sulfate. After filtration and concentration the residue was purified by Biotage (SNAP NH 28 g, EtOH:DCM) to give the title compound (91 mg, 69%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16034-46-1, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GRAHAM, Keith; KLAR, Ulrich; BRIEM, Hans; SIEMEISTER, Gerhard; MOeNNING, Ursula; (145 pag.)WO2017/21348; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 51516-70-2, These common heterocyclic compound, 51516-70-2, name is 5-Amino-1-(4-fluorophenyl)-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.

General procedure: Equimolar portionsof the intermediate compounds 1 (1 mmol) and the intermediatecompounds 3 (1 mmol) were dissolved in approximately 8 mL ofethanol. The reaction solution was allowed to stir at 80 8C for 2 huntil the reaction was complete. The reaction was monitored byTLC. Mostly, a precipitate formed and was then collected by suctionfiltration.

The synthetic route of 51516-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Xian-Hai; Ren, Zi-Li; Li, Dong-Dong; Ruan, Ban-Feng; Li, Qing-Shan; Chu, Ming-Jie; Ai, Cheng-Ying; Liu, Dao-Hong; Mo, Kai; Cao, Hai-Qun; Chinese Chemical Letters; vol. 28; 2; (2017); p. 377 – 382;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 35100-92-6, 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 35100-92-6 as follows.

6- (4 – ((2,5-dichloro-4-yl) amino) piperidin-1-yl) -3-cyano-pyridine (100mg, 0.286mmol) in n-butanol (5mL) solution of was added 1,5-dimethyl -1H- pyrazol-3-amine (40mg, 0.41mmol) and trifluoroacetic acid (212muL, 2.86mmol). The resultant reaction system was heated up to 120 deg.] C, sealed tube for 24 hours, until the reaction system was cooled to room temperature, concentrated under reduced pressure. To the resulting residue was added ethyl acetate (50 mL) was diluted and washed with water (15mL × 3) washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography Analysis (DCM / EtOAc / MeOH (v / v / v) = 25/5/1) to give the title compound as a whiteSolid (53mg, 44% yield)

According to the analysis of related databases, 35100-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Xi, Ning; Li, Minxiong; Li, Xiaobo; Dai, Weilong; Hu, Haiyang; Zhang, Tao; Chen, Wuhong; (105 pag.)CN105461694; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3112-31-0, 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 3112-31-0 as follows.

General procedure: Pyrazole-3,5-dicarboxylic acid (0.348 g, 2 mmol) and0.168 g piperazine (2 mmol) were dissolved in 20 cm3distilled water. The mixture was stirred for 1 h at room temperature. Then metal salts, 0.291 g nickel(II) nitratehexahydrate (1 mmol) for 1 and 0.169 g manganese(II)sulfate tetrahydrate (1 mmol) for 2 were added into the above-mentioned solution. The reaction mixture was refluxed for 3 h. It was then gradually cooled to room temperature and kept until crystals suitable for X-ray diffraction were obtained.

According to the analysis of related databases, 3112-31-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sharif, Mahboubeh A.; Najafi, Gholam Reza; Monatshefte fur Chemie; vol. 147; 9; (2016); p. 1557 – 1563;,
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 4522-35-4 as follows. Recommanded Product: 4522-35-4

NaH (60% dispersion in mineral oil, 143 mg, 3.57 mmol) was added to a stirred solution of 3-iodo-lH-pyrazole [4522-35-4] (659 mg, 4.00 mmol) in DMF (20 mL) at 0 C under N2 atmosphere. The mixture was stirred at room temperature for 30 min. 2- (Trimethylsilyl)ethoxymethyl chloride [76513-69-4] (0.66 mL, 3.74 mmol) was added at 0 C and the reaction mixture was stirred at room temperature for 16 h. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in heptane, gradient from 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to afford a mixture of 1-188 and 1-189 (965 mg, 86%).; Cul (28.3 mg, 0.15 mmol), N,N?-dimethylcyclo hexane- 1, 2-diamine (46.9 uL, 0.30 mmol) and K2C03 (411 mg, 2.98 mmol) were added to a solution of 1-188 and 1-189 (965 mg, 2.98 mmol) in l,4-dioxane (10 mL) in a sealed tube while nitrogen was bubbling. After 10 min, 4-chloro-lH-pyrrolo[3,2-c]pyridine [60290-21-3] (227 mg, 1.49 mmol) was added. The reaction mixture was stirred at room temperature for 10 min, and at 100 C for 20 h. The mixture was diluted with water and extracted with EtOAc. The combined organic extarcts were dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in heptane, gradient from 0/100 to 15/85). The desired fractions were collected and concentrated in vacuo to afford a mixture of 1-190 and I- 191 (270 mg, 51%).

According to the analysis of related databases, 4522-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 112029-98-8, 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. 112029-98-8 name is (1-Methyl-1H-pyrazol-4-yl)methanol, 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.

Under a stream of nitrogen, cyanomethylenetributylphosphorane (0.06 mL) was dropped into a 0.2-mL toluene solution of the compound (30 mg) produced in Reference Example 20 and (1-methylpyrazol-4-yl)methanol (9.6 mg), and the mixture was stirred overnight at 100C. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (7 mg) having the following physical property values. 1H-NMR (CDCl3): delta 1.26, 1.39-1.42, 1.68-1.85, 2.28-2.51, 2.55-2.65, 2.83-3.05, 3.87-4.01, 4.04-4.18, 4.89, 6.40, 6.72-6.79, 7.06-7.38, 7.41, 7.51, 8.77, 9.13.

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

Reference:
Patent; Ono Pharmaceutical Co., Ltd.; YOSHIDA, Takao; SHOYAMA, Akiko; TAKANO, Hirotsugu; (103 pag.)EP3482760; (2019); 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 288-13-1 as follows. Quality Control of 1H-Pyrazole

Step 1: Preparation of 3-pyrazol-1-yl-pyridine To a solution of 3-bromopyridine (5 g, 0.031 mol) in 50 ml of acetonitrile were added pyrazole (2.6 g, 0.038 mol), Cs2CO3 (16.5 g, 0.050 mol), Cu2O (0.226 g, 0.0016 mol), and salicylaldoxime (0.867 g, 0.006 mol) under N2 atmosphere. The reaction mass was refluxed for 24 hrs at 80 C. The reaction mass was concentrated and the crude was purified by column chromatography using ethyl acetate and hexane (1:1) to afford the pyrazolyl pyridine as a dark brown liquid (2 g, 43%): 1H NMR (400 MHz, CDCl3) delta 8.99 (d, J=2.8 Hz, 1H), 8.48 (dd, J=4.8, 1.2 Hz, 1H), 8.11-8.08 (m, 1H), 7.99 (d, J=1.2 Hz, 1H), 7.78 (d, J=1.2 Hz, 1H), 7.38-7.35 (m, 1H), 6.53 (t, J=1.2 Hz, 1H); MS (m/z) 146 [M+1].

According to the analysis of related databases, 288-13-1, the application of this compound in the production field has become more and more popular.

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 I.; Patny, Akshay; Garizi, Negar; LePlae, JR., Paul Renee; Wessels, Frank J.; Ross, JR., Ronald; DeAmicis, Carl; Borromeo, Peter; (118 pag.)US2016/60245; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 285984-25-0,Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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.

Step 2: Synthesis of N-l-(2-(bromomethvnbenzyl>3-(3-tert-butyl-l-P-tolyl-lH- pyrazoI-S-vDnrea.2-(Bromomethyl)benzaldehyde (0.23 g, 1.15 mmol) was dissolved in toluene (30 mL). 3-te/t-Butyl-l-p-tolyl-lH-pyrazol-5-amine (0.158 g, 0.578 mmol), triethylsilane (0.37 mL, 0.269 g, 2.30 mmol), and trifluoroacetic acid (0.222 mL, 0.341 g, 2.99 mmol) were added. The reaction was stirred at 65 0C for five hours. It was allowed to cool to room temperature. Ethyl acetate (50 mL) was added and it was extracted with NaHCO3 (aq.) (50 mL) and H2O (50 mL). The organic phase was dried over MgSO4, filtered, and evaporated. The crude product was purified by flash column chromatography. The resulting solid was recrystallized from ethyl acetate / hexane. (0.140 g, 53 %). IHNMR (400 MHz5 DMSO-J6) delta ppm 1.22 (s, 9H) 2.33 (s, 3H) 4.35 (d, J=5.64 Hz, 2H) 4.74 (s, 2H) 6.25 (s, IH) 6.95 (t, J=5.50 Hz, IH) 7.15-7.35 (m, 7H) 7.34-7.46 (m, IH) 8.21 (s, IH) HRMS (m/z) 455.1444. M+H, C23H27BrN4O requires 455.1441.

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-(p-tolyl)-1H-pyrazol-5-amine, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/91176; (2007); 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. 3469-69-0, name is 4-Iodopyrazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 3469-69-0

To a solution of 4-iodopyrazole (1.3 g, 6.8 mmol) in dioxane (10 mL) was added iodomethane (0.42 mL, 6.8 mmol) and the resulting mixture stirred at room temperature for 96 h. The mixture was concentrated in vacuo and the residue mixed with methylene chloride and filtered. The filtrate was concentrated in vacuo to provide 1.35 g (95%) of the title compound as a colorless oil. 1H NMR (CDCl3) delta 7.47 (s, 1H), 7.38 (s, 1H), 3.90 (s, 3H).

According to the analysis of related databases, 3469-69-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US6797723; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics