Day: September 1, 2021

Electric Literature of 35344-95-7, These common heterocyclic compound, 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, 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.

A nucleophile (1 mmol)was added to a solution of compound 1 or 2 (1 mmol) in MeCN or EtOH(10 ml) and the mixture was stirred at room temperature for 30 min (foradducts with 1) or 2?24 h (for adducts with 2). The precipitated productwas filtered off, washed with the same solvent (5 ml) and dried in air to give beige or brown solid adduct.

Statistics shows that 1H-Pyrazole-4-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 35344-95-7.

Reference:
Article; Starosotnikov, Alexey M.; Shkaev, Dmitry V.; Bastrakov, Maxim A.; Fedyanin, Ivan V.; Shevelev, Svyatoslav A.; Dalinger, Igor L.; Mendeleev Communications; vol. 28; 6; (2018); p. 638 – 640;,
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. 400755-44-4, name is 1-Ethylpyrazole-3-carboxylic Acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2O2

To 1 -ethyl- 1H- pyrazole-3-carboxylic acid (5.01 g, 35.7 mmol) in benzene/MeOH (45 mL/10 mL) at 0 C was added drop wise (diazomethyl)trimethylsilane (19.7 mL, 39.3 mmol) in hexanes (2M). The cold bath was removed and the reaction mixture was stirred at ambient temperature for one hour. The reaction was quenched with the addition of acetic acid (0.25 mL). The mixture was concentrated under reduced pressure to give crude product, to which was added THF (50 mL) and the solution was cooled to 0 C. Lithium aluminum hydride (1.36 g, 35.7 mmol) was added cautiously to the solution. The cold bath was removed once the addition was complete. The mixture was stirred at ambient temperature for 2 hours and the reaction was quenched by careful addition of sodium sulfate decahydrate. The mixture was filtered through Celite, and the filter pad was washed with EtOAc (200 mL). The filtrate was concentrated under reduced pressure to give the product (4.41 g).

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; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BRADLEY, Michael; DELISLE, Robert Kirk; HENNINGS, D. David; KENNEDY, April L.; MARMSATER, Fredrik P.; MEDINA, Matthew; MUNSON, Mark C.; RAST, Bryson; RIZZI, James P.; RODRIGUEZ, Martha E.; TOPALOV, George T.; ZHAO, Qian; WO2011/79076; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 360056-45-7, 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. 360056-45-7, name is Methyl 4-amino-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of 4-amino-1/-/-pyrazole-3-carboxylic acid methyl ester (0.634 Kg, 4.49 mol, 1 wt) in 1 ,4-dioxane (8.90 L, 9 vol) under nitrogen was treated with triethylamine (0.761 L, 5.46 mol, 1.2 vol) followed by 2,6-dichlorobenzoyl chloride (0.710 L, 4.96 mol, 0.72 vol) such that the internal temperature was maintained in the range 20 to 25 0C. Residual 2,6- dichlorobenzoyl chloride was washed in with a line rinse of 1 ,4-dioxane (0.990 L, 1 vol) and the reaction mixture stirred at 18 to 25 C until complete (16 hours) by TLC analysis (eluent: ethyl acetate: heptanes 3:1 ; Rfamine0.25, Rf product0.65). The reaction mixture was filtered, the filter-cake washed with 1 ,4-dioxane (2x 0.990 L, 2x 1 vol) and the combined filtrates (red) progressed to Stage 4 without further isolation. Stage 3: Preparation of 4-(2,beta-dichlorobenzoylamino)-1 H-pyrazole-3-carboxvlic acid methyl esterTriethylamine (1.42L, 10.20 MoI, 1.2 vol) was added to solution of 4-amino-1H-pyrazole-3- carboxylic acid methyl ester (1.184Kg, 8.39 MoI, 1.0 wt) in 1 ,4-dioxane (10.66L, 9.0 vol) at 15 to 250C under nitrogen. 2,6-Dichlorobenzoyl chloride (1.33L1 9.28 MoI1 1.12 vol) was charged at 15 to 25C followed by a line rinse of 1 ,4-dioxane (1.18L, 1.0 vol) and the reaction mixture stirred at 15 to 25C for 14 to 24 hours. Reaction completion was determined by 1H NMR analysis1. The reaction mixture was filtered, the filter-cake washed with 1 ,4-dioxane (2x 1.18L, 2x 1.0 vol) and the combined filtrates progressed to Stage 4 without further isolation.

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, Methyl 4-amino-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/9954; (2008); 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. 478968-48-8, name is Ethyl 3-methoxy-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Ethyl 3-methoxy-1H-pyrazole-4-carboxylate

A mixture of CuT (88 mg, 0.46 mmol, 0.10 equiv), L-proline (108 mg, 0.94 mmol, 0.20 equiv), potassium carbonate (1.3 g, 9.41 mmol, 2.00 equiv), ethyl 3-methoxy-1H-pyrazole-4-carboxylate (800 mg, 4.70 mmol, 1.00 equiv), and 5-bromo-2-(trifluoromethyl)pyrimidine (1.28 g, 5.64 mmol, 1.20 equiv) in DMSO (5 mL) was stirred overnight at 100C under nitrogen. The reaction mixture was diluted with 40 mL of water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:5) to afford the title compound (580mg, 39%) as a white solid.

According to the analysis of related databases, 478968-48-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; CHU, Yanyan; DO, Steven; ESTRADA, Anthony; HU, Baihua; KOLESNIKOV, Aleksandr; LIN, Xingyu; LYSSIKATOS, Joseph P.; SHORE, Daniel; VERMA, Vishal; WANG, Lan; WU, Guosheng; YUEN, Po-wai; WO2015/52264; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, 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. HPLC of Formula: C8H14N4O

To a 250 ml three-necked flask was added 8.15 g of 2-ethoxybenzaldehyde, 9.6 g of 1-methyl-3-propyl-4-aminopyrazole-5-carboxamide and 150 ml of isopropanol, 3 hours; to the reaction system into the oxygen, add 8.56g anhydrous ferric chloride, temperature 60 C reaction 3 hours; reaction is completed, add 180ml of purified water, cooled to room temperature filtration, drying solid 15.78. Yield:

The synthetic route of 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Tongjuan Pharmaceutical Technology Co., Ltd.; Zheng Qingquan; Huang Shifu; Cao Xutao; Li Yongjian; (10 pag.)CN104804003; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 31108-57-3, 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.

General procedure: To a solution of II-M1 (510 mg, 1.19 mmol) in Acetone (10 mL) was added K2C03 (245 mg, 1.78 mmol) and 5-methyl-2H-tetrazole (211 mg, 1.42 mmol) at 20C. The mixture was stirred at 20C for 16 hrs. The reaction mixture was treated with water (20 mL). The mixture was extracted with EtOAc (2 x 20 mL). The combined organic phase was washed with brine (20 mL), dried over anhydrous Na2S04, filtered, concentrated in vacuum. The residue was purified by HPLC (Column: YMC-Actus Triart C18 l00*30mm*5um), gradient: 75-95% B (water (0.05%HCl)-ACN), flow rate: 25 mL/min) to afford the mixture II-M2 and II-M2a (Peak 1, 320 mg, ) as a solid and IJ~M2b (Peak 2, 50 mg, ) as a solid. (0920) The mixture II-M2 and II~M2a (320 mg, ) was purified by SFC (column: DAICEL (0921) CHIRALCEL OJ-H(250mm*30mm,5um)), gradient: 35-35% B (0. l%NH3H2O, B= EtOH ), flow rate: 200 mL/min) to afford II-M2 (Peak 1, 49 mg, 8 %) as a solid and II-M2a (Peak 2, 62 mg, 10 %) as a solid. (0922) The residue II-M2b (50 mg, ) was dissolved in MeCN (5 mL) at 25C and concentrated in vacuum to II~M2b (45 mg, 8 %) as a solid.

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

Reference:
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, G.; BLANCO-PILLADO, Maria, Jesus; LA, Daniel; HARRISON, Boyd, L.; (276 pag.)WO2019/126741; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1105039-93-7, 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 1105039-93-7 as follows.

A solution of l-(4-methoxybenzyl)-lH-pyrazole-4- carboxylic acid (34.4 mmol, 8.00 g), oxalyl chloride (68.9 mmol, 5.92 mL) and a drop of DMF in DCM (80 mL) was stirred for 1 h at rt. After evaporation, the crude product was dissolved in DCM (30 mL) and was added at 0C to a solution of Nu,Omicron- dimethylhydroxylamine hydrochloride (103 mmol, 6.31 g) in DCM (100 mL), followed by Et3N (138 mmol, 19.2 mL). The reaction mixture was stirred for 1 h at rt. The reaction was quenched with a saturated aqueous solution of Na2C03 (300 mL) and the aqueous phase was extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated to dryness to yield the title compound (33.8 mmol, 9.30 g, 98%) as a beige solid.UPLC-MS: RT = 0.72 min; MS m/z ES+= 276.

According to the analysis of related databases, 1105039-93-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADDEX PHARMA S.A.; JONES, Philip; MERCK SHARP & DOHME CORP.; TANG, Lam; BOLEA, Christelle; CELANIRE, Sylvain; LIVERTON, Nigel, J.; WO2012/9001; (2012); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 4149-06-8, The chemical industry reduces the impact on the environment during synthesis 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, I believe this compound will play a more active role in future production and life.

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

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-Amino-1-phenyl-1H-pyrazol-5(4H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
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. 13599-12-7, name is Ethyl 3-phenyl-1H-pyrazole-5-carboxylate, A new synthetic method of this compound is introduced below., name: Ethyl 3-phenyl-1H-pyrazole-5-carboxylate

A mixture of ethyl 3-phenyl-lH-pyrazole-5-carboxylate (70.0′ g) , 2, 4-dichlorobenzyl chloride (69.6 g) , potassium carbonate (53.7 g) and N,N-dimethylformamide (400 ml) was stirred at room temperature for 15 hr, the reaction mixture was concentrated, and the residue was partitioned between water and ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSCU) / and concentrated. The residue was crystallized from ethyl acetate- hexane to give ethyl 1- (2, 4-dichlorobenzyl) -3-phenyl-lH- pyrazole-5-carboxylate (61.0 g, yield: 50%) as brown crystals, melting point 104-1070C.

The synthetic route of 13599-12-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/18314; (2007); A2;,
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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H6N2O

Step 2: 1 – methyl – l H-pyrazole-4-carbaldehyde oxime A mixture of the combined organic layer having 1 -methyl- l H-pyrazole-4-carbaldehyde and ethyl acetate obtained from step 1 , hydroxylamine hydrochloride (63.48 gm, 0.9135 moles) were refluxed at 70-80C for 2-4 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-5C, to this added DM water ( 100 ml) and 25% aqueous ammonia solution (100 ml) at 0-5C. The reaction mixture was stirred for 10 min at 20-30C. The organic layer was separated and aqueous layer was extracted with ethyl acetate (250 ml). The entire organic layer was transferred to the reaction vessel and washed with 10% brine solution (500 ml). Stirred for 10 min and separated the final aqueous layer and organic layer. The organic layer was evaporated to obtain the 1 -methyl- lH-pyrazole-4- carbaldehyde oxime. Dry wt : 60 gm Yield : 1.2 w/w (79%) HPLC purity : 99.78%

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 25016-11-9.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M.; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2111; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics