Day: May 14, 2021

1269293-48-2, name is Ethyl 5-bromo-1-methyl-1H-pyrazole-3-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. Formula: C7H9BrN2O2

A mixture of ethyl 5-bromo-1-methyl-pyrazole-3-carboxylate (300 mg, 1.29 mmol) and methanamine in MeOH (10 mL, 12.87 mmol) was heated to 80 C. and stirred overnight. The reaction solution was concentrated to give the product 5-bromo-N,1-dimethyl-pyrazole-3-carboxamide (280 mg, 99% yield) as a colorless oil. LCMS (ESI) [M+H]+=218.2

The synthetic route of 1269293-48-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 75092-30-7, The chemical industry reduces the impact on the environment during synthesis 75092-30-7, name is 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid, I believe this compound will play a more active role in future production and life.

A round-bottom flash was charged with 4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid (297 g, 1.18 mol), DCM (2.97 L), and 1,1?-carbonyldiimidazole (CDI) (207 g, 97% by mass, 1.24 mol). The reaction mixture was stirred at room temperature for 45 min. Ammonium chloride (189 g, 3.53 mol) and triethylamine (498 mL, 3.53 mol) were added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was suspended in H2O (3 L) and granulated at room temperature for 1 h. The solid was collected via filtration, washed with H2O, and dried in a vacuum oven to afford 4-iodo-1-methyl-1H-pyrazole-5-carboxamide as a colorless solid (222 g, 75% yield). 1H NMR (CDCl3) delta: 7.53 (s, 1H), 6.56 (br s, 1H), 6.01 (br s, 1H), 4.21 (s, 3H). UPLC (UPLC-MS Method 1): tR=0.15 min. MS (ES+): 251.1 (M+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, 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; Darout, Etzer; Dullea, Robert; Hawkins, Julie Jia Li; Londregan, Allyn T.; Loria, Paula M.; Maguire, Bruce; McClure, Kim F.; Petersen, Donna N.; Piotrowski, David W.; US2014/315928; (2014); 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. 149978-43-8, name is 2-Methyl-5-trifluoromethyl-2H-pyrazol-3-ylamine, A new synthetic method of this compound is introduced below., Safety of 2-Methyl-5-trifluoromethyl-2H-pyrazol-3-ylamine

EXAMPLES EXAMPLE 1 5-(2-chloro-6-fluorophenyl)-N-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]-1H-pyrazole-3-carboxamide [0112] Compound of Preparation 3 (100 mg, 0.42 mmol) and 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-amine (76 mg, 0.46 mmol) were dissolved in 1.5 mL DMF. N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride 98% (62 mg, 0.46 mmol) and 1-Hydroxybenzotriazole hydrate (88 mg, 0.46 mmol) were added and the mixture was stirred at room temperature for 7 days. Dichloromethane was added and the organic phase was washed with water two times, saturated aqueous NaHCO3 solution and brine, dried over MgSO4 and evaporated under reduced pressure and the residue was purified using the Isolera purification (diethyl ether – hexane gradient, 0:100 rising to 100:0) to give 54 mg (0.13 mmol, 33%) of the title compound as a white solid. LRMS (m/z): 388 (M+1)+. 1 H NMR (300 MHz, CHLOROFORM-d) d ppm 3.90 (3 H, s), 6.69 (1 H, s), 7.11 – 7.23 (1 H, m), 7.33 – 7.45 (2 H, m), 8.69 (1 H, br. s)

The synthetic route of 149978-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Almirall, S.A.; GONZALEZ RODRIGUEZ, JACOB; VIDAL JUAN, BERNAT; GUAL ROIG, SILVIA; EP2848615; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 873191-23-2, The chemical industry reduces the impact on the environment during synthesis 873191-23-2, name is 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

General procedure: The lycorine derivatives 10, 11 and 12 (0.1mmol) were dissolved in dry THF (10mL), and NaH (50mg, 2mmol) and 3-(bromomethyl)pyridine, 3-(Chloromethyl)-1,5-dimethyl-1H-pyrazole or 5-Bromomethyl-1,3-dimethyl-1H-pyrazole (1mmol) were added. The mixture was stirred at r. t. for 24h and quenched with H2O (50mL) in an ice bath. The solution was evaporated to remove the THF and extracted with CH2Cl2 (2×30mL). The organic layer was washed with saturated NaHCO3 and brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using petroleum ether-EtOAc as the eluent to afford compounds 5, 6, 7, 8 and 9. 8-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-5-ethyl-4-methyl-5,6-dihydro- phenanthridine (5). 78% yield. Colorless amorphous powder (from CH2Cl2); 1H NMR (500MHz, CDCl3) delta 7.59 (d, J=8.5Hz, 1H), 7.50 (d, J=7.6Hz, 1H), 7.06 (d, J=8.0Hz, 1H), 7.00 (t, J=7.5Hz, 1H), 6.86 (dd, J=8.5, 2.6Hz, 1H), 6.74 (d, J=2.5Hz, 1H), 6.04 (s, 1H), 4.94 (s, 2H), 4.01 (s, 2H), 3.79 (s, 3H), 2.62 (q, J=7.1Hz, 2H), 2.29 (s, 3H), 2.19 (s, 3H), 1.01 (t, J=7.1Hz, 3H); 13C NMR (125MHz, CDCl3) delta 157.77 (C), 147.36 (C), 146.31 (C), 137.89 (C), 135.20 (C), 133.43 (C), 129.94 (CH), 129.12 (C), 126.72 (C), 124.38 (CH), 123.89 (CH), 120.90 (CH), 113.66 (CH), 112.84 (CH), 106.77 (CH), 60.61 (CH2), 50.18 (CH2), 46.12 (CH2), 36.50 (CH3), 17.79 (CH3), 13.63 (CH3), 13.43 (CH3); HRESIMS m/z 348.2055 [M+H]+ (calcd for C22H26N3O, 348.2070).

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, 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Duozhi; Zhang, Heng; Jing, Chenxu; He, Xiaoli; Yang, Bijuan; Cai, Jieyun; Zhou, Yunfu; Song, Xiaoming; Li, Lin; Hao, Xiaojiang; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 1491 – 1499;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 28466-62-8,Some common heterocyclic compound, 28466-62-8, name is 1-Benzyl-1H-pyrazol-4-amine, molecular formula is C10H11N3, 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 -(2-trimethylsilanyl-ethoxymethyl)-1 ,2-dihydro-pyridin-3-yl]-indole-1 -carboxylic acid tert-butyl ester, (1g, 1.46mmol), benzyl-1 H-pyrazole-4-yl amine (0.75g, 4.39mmol), 1- hydroxybenzotriazole hydrate (0.59 g, 4.39 mmol) and tetrahydrofuran (15ml_) were placed in a microwave vial. To this solution was added N,N-diisopropylethylamine (0.58g, 0.78mL, 4.49mmol) and N-p-dimethylaminopropyO-N’-ethylcarbodiimide hydrochloride (0.84g, 4.39mmol), the vial capped and heated in the microwave at 90 0C for 30 minutes. After cooling, the mixture was concentrated in vacuo and the residue partitioned between water and dichloromethane. The organic layer was separated and the aqueous was extracted with a further portion of dichloromethane. The combined dichloromethane layers were dried (Na2SO4) and concentrated in vacuo. The resultant crude product was purified by flash chromatography on SiO2 eluting with dichloromethane – 15% methanol / dichloromethane (gradient) to afford the desired title compound as a yellow foam, 1.Og, 82%.

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

Reference:
Patent; VERNALIS (R & D) LTD; WO2009/93012; (2009); 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 1125828-26-3 as follows. Recommanded Product: 1-(2-Bromo-5-chlorophenyl)-3-methyl-1H-pyrazole

The above THF solution was transferred to a jacketed 3L 3-neck round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet. After diluting with THF (800 mL), the water content in the solution was checked by KF (0.053%). To the above solution was added a solution of i-PrMgCl in THF (Aldrich 2 M, 286 mL, 0.572 mol) at 0-10 C. over 1 hours. The resulting solution was stirred for 30 minutes at 10 C. (GC showed the completion of magnesium-bromine exchange reaction). Ethyl trifluoroacetate (74 mL, 0.620 mol) was then added to the Grignard solution between -20 and -10 C. over 45 minutes, slowly warmed to 0 C., and stirred for 30 minutes at the same temperature. The reaction mixture was poured into 2 N HCl (300 mL) at 0 C., and stirred for 30 minutes at room temperature. The organic layer was diluted with MTBE (500 mL), and washed with brine (250 mL) followed by water (250 mL). Solution assay of organic layer was carried out using GC (Compound 5: 67% solution yield, the corresponding regioisomer 6 was present at about 20% relative to 5). The solution was then concentrated under vacuum to 2× solution. To remove water, THF (500 mL) was added, and evaporated to 2× solution. THF addition-concentration was repeated to give a 2× solution. Heptane (500 mL) was added, concentrated to 2× solution to exchange the solvent for recrystallization. Heptane (500 mL) was again added, concentrated to 3.5× solution.The 3.5× heptane solution was then transferred to a 1L 3-neck jacketed round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet. The solution was heated at 60 C., and the resulting homogeneous solution was slowly (1-2 h) cooled to room temperature with stirring, further cooled to 0 C. and stirred for 30 minutes at the same temperature. The crystals were collected and washed with ice-cold heptane (200 mL), dried under vacuum at 50 C. to afford a pale yellow solid (Compound 5, 85.7 g, 99% pure by GC, 62% yield from fluoride 1). M.p.: 83 C. (DSC onset temperature) 1H NMR (400 MHz, CDCl3) delta 7.85 (1H, d, J=2.5 Hz), 7.48 (1H, d, J=1.7 Hz), 7.38 (1H, d, J=8.3 Hz), 7.31 (1H, dd, J=8.1, 1.8 Hz), 6.33 (1H, d, J=2.5 Hz), 2.30 (3H, s); 13C NMR (100 MHz, CDCl3) delta 184.2 (q, JC-F=36.6 Hz), 151.7, 138.7, 138.5, 130.7, 126.4, 125.7, 124.5, 116.8, 116.1 (q, JC-F=289.8 Hz), 109.7, 13.0; 19F NMR (376 MHz, CDCl3) delta=-76.8 (s).

According to the analysis of related databases, 1125828-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bednarz, Mark S.; Burgoon, JR., Hugh Alfred; Iimura, Shinya; Kanamarlapudi, Ramanaiah C.; Song, Qiuling; Wu, Wenxue; Yan, Jie; Zhang, Haiming; US2009/62540; (2009); 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. 73387-52-7, name is 5-(4-Bromophenyl)-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 73387-52-7

5-(4-bromophenyl)-1 -methyl-1 H-pyrazole (7.84 g), sodium te/f-butoxide (3.81 g), 1 ,1 ‘-bus(di-i-propylphosphino)ferrocene (332 mg), and palladium acetate (148 mg ) were placed under nitrogen and combined with 60 ml_ anhydrous 1 ,4-dioxane. The resulting mixture was stirred at room temperature for 1 hour before adding thisopropylsilanethiol (7.81 ml) followed by heating at reflux for 1 hour. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water twice and 5% aqueous sodium chloride once. The organic layer was dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography on silica gel to give the title compound. LCMS (M+H): 347; 1 H NMR (400 MHz, DMSO-c/6) delta ppm 0.85- 0.96 (m, 3 H) 0.96 – 1.02 (m, 18 H) 3.84 (s, 3 H) 7.40 (s, 1 H) 7.46 (s, 1 H) 7.58 (d, J=8.32 Hz, 2 H) 7.63 – 7.71 (m, 2 H).

The synthetic route of 73387-52-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/69044; (2009); 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. 15001-11-3, name is Ethyl 5-amino-1-(p-tolyl)-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

The synthetic route of 15001-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 143426-49-7, A common heterocyclic compound, 143426-49-7, name is (4-Pyrazol-1-yl-phenyl)methanol, molecular formula is C10H10N2O, 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.

Example 4 N-[1-(6-{[4-(1H-pyrazol-1-yl)benzyl]oxy}-1-benzofuran-3-yl)ethyl]acetamide To a solution of N-[1-(6-hydroxy-1-benzofuran-3-yl)ethyl]acetamide (35.0 mg, 0.160 mmol) obtained in Reference Example 4 in THF (5 mL) were added [4-(1H-pyrazol-1-yl)phenyl]methanol (41.8 mg, 0.240 mmol), triphenylphosphine (63.0 mg, 0.240 mmol) and 2.2 M diethyl azodicarboxylate toluene solution (0.110 mL, 0.240 mmol), and the mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure and the obtained residue was purified by preparative HPLC to give the title compound (29.4 mg, yield 33%) as a white solid. preparation system: Waters large scale preparation system (UV Purification System)

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; Takeda Pharmaceutical Company Limited; EP2351743; (2011); 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. 796729-03-8, name is 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Safety of 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid

Add 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid (1.60 g, 10.5 mmol) and 30 mL of 1,4-dioxane, benzyl alcohol to a 50 mL vial (1.64 mL, 15.8 mmol), DIPEA (3.5 mL, 21.0 mmol),And DPPA (4.35g, 15.8mmol), reacted at 105 C for 3h, the reaction was completed by TLC, directly spin-drying silica gel column chromatography, eluting with PE / EA = 2 / 1 to obtain 0.35g white solid, yield 13 %,

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Lin Xinglong; Xie Hongming; Hu Yangxiao; Li Shiguang; Zhang Yingjun; Tan Yumei; Yuan Mingyun; (124 pag.)CN108948019; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics