Day: June 15, 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. 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. Product Details of 360056-45-7

Reference Example 10 4-amino-N-methyl-1H-pyrazole-3-carboxamide A mixture of methyl 4-amino-1H-pyrazole-3-carboxylate obtained in Reference Example 2 (5.39 g, 38.2 mmol) and 40% methylamine/methanol solution (25 mL) was stirred at room temperature for 2 days. The mixture was concentrated under reduced pressure. Then methanol was added to the residue, and the mixture was concentrated under reduced pressure, the operation was twice repeated. Methanol and activated carbon (4.5 g) were added to the residue. After filtration, the solvent was evaporated under reduced pressure to give the title compound (5.31 g, yield 99%). 1H-NMR (DMSO-d6, 200 MHz): delta 2.71 (3H, d, J=4.8 Hz), 4.58 (2H, brs), 7.09 (1H, s), 7.72-7.86 (1H, brm).

The synthetic route of 360056-45-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tsukamoto, Tetsuya; Yamamoto, Takeshi; Tokunoh, Ryosuke; Kawamoto, Tomohiro; Okura, Masahiro; Kori, Masakumi; Murase, Katsuhito; US2009/156582; (2009); A1;,
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. Recommanded Product: 3-Methylpyrazole

General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999percent purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98percent purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of known products was confirmed by 1H and 13C NMR spectroscopic analysis.

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:
Article; Teo, Yong-Chua; Yong, Fui-Fong; Lim, Gina Shiyun; Tetrahedron Letters; vol. 52; 52; (2011); p. 7171 – 7174;,
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. 2075-46-9, name is 4-Nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Nitro-1H-pyrazole

A solution of 4-nitropyrazole (300 rro, 0.27 mmol, I eq.), 2-bromoethanol (206 4,0.29 mmol, 1.1 eq.) and K2C03 (549 mg, 0.40 mmol, 1.5 eq.) in CH3CN (5mL) was heated to 80 C for 18 h. The mixiure was allowed to cool and parlitioned between EtOAc (3 x 30 mL) and water (20 mL). The organic layers were dried over MgSO4, evaporated, and the residue purified by MPLC on SiC2 with gradient elution from 30-60% EtOAc/petrolto give 2-(4-Nitro-IH-pyrazol-1- y[)ethanol as a white solid (256 mg, 61%).

The synthetic route of 2075-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; REUILLON, Tristan; MILLER, Duncan; MYERS, Stephanie; MOLYNEUX, Lauren; CANO, Celine; HARDCASTLE, Ian; RIGOREAU, Laurent; GOLDING, Bernard; NOBLE, Martin; (246 pag.)WO2016/42341; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 288-13-1, 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. 288-13-1 name is 1H-Pyrazole, 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.

General procedure: Complex 2 (0.05 mmol) was added to a 5 mL of a sealed tube containing the aryl iodide or bromide (0.5 mmol), 1H-pyrazole (0.75 mmol), NaOH (1 mmol), and DMSO (1 mL). The mixture was stirred at 100 C for 12 h. After being cooled to room temperature, the mixture was quenched with 10 mL H2O and extracted with EtOAc(3 × 20 mL). The combined EtOAc extracts were dried with anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure.The residue was purified by flash column chromatography on silicagel with PE/EtOAc (from 10:1 to 5:1) as the eluent to afford the pure products. All N-aryl pyrazoles reported here are known products and were characterised by 1H NMR, and GC-MS.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Pyrazole, and friends who are interested can also refer to it.

Reference:
Article; Liu, Yan; Liu, Wei; Zhang, Qin; Liu, Ping; Xie, Jian-Wei; Dai, Bin; Journal of Chemical Research; vol. 37; 10; (2013); p. 636 – 637;,
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 1280210-79-8 as follows. Formula: C10H15N3O2

Step 2. A solution of tert-butyl 2H,4H,5H,6H-pyrrolo[3,4-c]pyrazole-5- carboxylate (250 mg, 1 . 1 mmol, 1 ,00 equiv) in DCM (5 mL) and TFA (5 mL) was stirred at rt overnight. The reaction mixture was concentrated under vacuum and the residue was redissolved in 20 mL of concentrated HC1 and then concentrated under vacuum again to yield 200 mg of crude 2H,4H,5H,6H-pyrrolo[3 ,4-c]pyrazole hydroch loride as a dark red sol id. LC/MS ( Method C, ESI): RT = 0.46 min, m z = 1 1 0.0 [M+H] .

According to the analysis of related databases, 1280210-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; DRAGOVICH, Peter; GOSSELIN, Francis; YUEN, Po-Wai; ZAK, Mark; ZHENG, Xiaozhang; WO2013/127267; (2013); 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 632365-54-9 as follows. Recommanded Product: 632365-54-9

To a refluxing mixture of 7.0 g (175 mmol) of sodium hydride (NaH 60% dispersion in mineral oil) and 10.45 g (88.5 mmol) [OF DIETHYL CARBO7LATE (CO (OETJ2)] in 100 mL of toluene was added dropwise via an addition funnel a mixture of 10 g [(44. 3] mmol) [OF 1- (4-BENZYLOXY-] [PHENYL)-ETHANO7LE] in 20 mL of toluene, and the resulting mixture was heated at reflux under argon for 1 h. The reaction mixture was then cooled to [0C,] quenched by the addition of 40 mL of acetic acid, during which time a yellow precipitate formed, and it dissolved upon subsequent addition of water. The separated organic layer was washed with saturated sodium bicarbonate solution, water and brine, dried over sodium sulfate and concentrated to give a residue which was chromatographed on silica gel (10% hexane in dichloromethane) to afford 9.2 g (70% yield) of desired [3-(4-BENZYLOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER] as indicated by 1H NMR. To a solution of 2 g (6.7 mmol) of 3-(4-benzyloxy-pyenyl)-3-oxo-propionic acid ethyl ester in 12 mL of ethanol (heated slightly for complete dissolution) was added dropwise 7 mL (7 mmol) [OF POTASSIUFN T-BUTOXIDE (KOTBU 1 MSOLUTION IN T-BUTANOL),] during which time a precipitate formed. The reaction mixture was stirred at rt for 20 min, then diethyl ether was added and the precipitate was collected by filtration, washed with ether and dried to afford 2.2 g (98% yield) of desired [3-(4-BENZYLOXY-PHE7LYL)-3-OXO-PROPIONIC ACID ETHYL ESTER POTASSIUM] salt as indicated by 1H NMR. A mixture 100 mg (0.3 mmol) of 3-(4-benzyloxy-phenyl)-3-oxo-propionic acid ethyl ester potassium salt, 86 mg (0.45 mmol) of 2-cyclohexylethyl bromide, and 17 mg (0.1 mmol) of potassium iodide (KI) in 1 mL [OF DIMETHYLFONNAMIDE (DMF)] in a 4 mL vial was shaken in a sand bath at [80 C] overnight. The mixture was then concentrated to give a residue which was purified via reverse-phase chromatography (Gilson) to afford (after lyophilization) 85 mg (70% yield) of 2- (4-benzyloxy-benzoyl)-4-cyclohexyl-butyric acid ethyl ester as a solid as indicated by LC-MS-calcd for [C26H3202 [M++H] +] : 409.23, found: 409.2. A mixture of 71 mg (0.171 mmol) [OF 2-(4-BENZYLOXY-BE7LZOYL)-4-CYCLOHEXYL-BUTYRIC ACID] ethyl ester, 24 mg (0.171 mmol) of [5-AMINO-1H-PYRAZOLE-3-CARBOXYLIC ACID METHYL ESTER,] 7 mg (20 [MOL%)] [OF P-TOLUEYLESULFOFZIC ACID MONOHYDRATE (PTSA),] and 3 mL of chlorobenzene was heated at [120 C] overnight. The reaction mixture was then concentrated to a residue which was purified via reverse-phase chromatography (Gilson) to afford (after lyophilization) desired 5-(4-benzyloxy-phenyl)-6-(2-cyclohexyl-ethyl)-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine- 2-carboxylic acid methyl ester as a solid as indicated by LC-MS-calcd for [C29H3LN304] [[M +H] +] : 486.23, found: 486.2. This material was then converted to 5-(4-benzyloxy-phenyl)- 6-(2-cyclohexyl-ethyl)-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (559) via the well known LiOH saponification protocol (10% yield over 2 steps); LC-MS-calcd for [C2SH29N304] [[M++H] +] : 472.22, found: 472.2. Note that the same synthetic sequence was carried out from the commercially available [3-FURAN-3-YL-3-OXO-PROPIONIC ACID ETHYL ESTER] as depicted above to give [6- (2-CYCLOHEXYL-ETHYL)-] 5-furan-3-yl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (612).

According to the analysis of related databases, 632365-54-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEOGENESIS PHARMACEUTICALS, INC.; WO2003/101993; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 2075-45-8, These common heterocyclic compound, 2075-45-8, name is 4-Bromo-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.

To a mixture of 4-bromo- lH-pyrazole (500 mg, 3.40 mmol) in DCM (10 mL) was added Boc20 (0.790 mL, 3.40 mmol) and Et3N (0.948 mL, 6.80 mmol). The mixture was stirred at 25 C for 1 h. The mixture was concentrated to afford fert-butyl 4-bromo- lH-pyrazole-l-carboxylate (800 mg, 2.91 mmol, 86% yield). TLC (PE/EA = 2: 1, Rf = 0.6): lH NMR (400 MHz, CD3OD) delta 8.31 (s, 1H), 7.77 (s, 1H), 1.63 (s, 9H). ES-LCMS m/z 148.0 (M-Boc+H).

Statistics shows that 4-Bromo-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 2075-45-8.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EIDAM, Hilary Schenck; DEMARTINO, Michael P.; GONG, Zhen; GUAN, Amy Huiping; RAHA, Kaushik; WU, Chengde; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; CHEUNG, Mui; WO2014/141187; (2014); 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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

General procedure: Under nitrogen atmosphere, carboxylic acid II (3mmol), EDCI (3.3 mmol), HOBT (3.3 mmol)and Et3N (1.8 mmol) were placed in a three-necked flask with 40 mL CH2Cl2, and stirred for 2 hat 0 C; then, compound I (2.4 mmol) was added to the flask and allowed to react for 3 h at 0 C.The reaction was monitored by thin-layer chromatography (TLC) (all reactions could be completed in3 h) and, on completion of the reaction, the mixture was washed with saturated NaHCO3 solutionand water, respectively. Then, it was dried over anhydrous Na2SO4, filtered and evaporated onrotavapor in vacuum. Subsequently, crude products III-1-III-18 were purified by silica gel columnchromatography [V (CH2Cl2): V (EA) = 3:1] and crude products III-19-III-36 were purified by silicagel column chromatography [V (PE): V (EA) = 3:1]. Finally, products were recrystallized with thedichloromethane/petroleum ether to obtain pure target compounds.

According to the analysis of related databases, 176969-34-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Shen; Meng, Siqi; Xie, Yong; Yang, Yonggui; Zhang, Yumeng; He, Lu; Wang, Kai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Li, Xinghai; Molecules; vol. 24; 14; (2019);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

5334-43-0, name is 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile, 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. Application In Synthesis of 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile

General procedure: (General method). Amixture of the appropriate aminonitrile 1 (3.0 mmol) and1,3-dicarbonyl compound (3.0 mmol) in anhydrous toluene(12 ml) was refluxed for 1 h in a flask equipped with aDean-Stark trap. Tin(IV) chloride (3.0 g, 11.5 mmol) wasadded to the reaction mixture, and refluxing was continuedfor additional 5-6 h. A resinous precipitate was formed,andthe colorless toluene layer was decanted. The residualsolvent was removed on a rotary evaporator, the obtainedglassy solids were dissolved in boiling dioxane, cooled, thenpoured into a solution of Na23 (4.0 g) in water (70 ml).The precipitate that formed was filtered off, washed withwater, dried, and recrystallized from a 5:1 mixture of2-PrOH-DMF.

The synthetic route of 5334-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Potapov, Andrei Yu.; Vandyshev, Dmitriy Yu.; Kosheleva, Yevgeniya A.; Polikarchuk, Vladimir A.; Potapov, Mikhail A.; Shikhaliev, Khidmet S.; Chemistry of Heterocyclic Compounds; vol. 53; 2; (2017); p. 207 – 212; Khim. Geterotsikl. Soedin.; vol. 53; 2; (2017); p. 207 – 212,6;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-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. Computed Properties of C10H15N3O2

INTERMEDIATE 4; Step A: fert-Butyl 2-(2-aniino-2-oxoemyl)-2,6-dihvdropvrrolof3,4-c|pyrazole-5(4H)- carboxylateA 2 L three neck flask fitted with a thermometer, a mechanical stirrer and an addition funnel was charged with a suspension of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole- 5(4H)-carboxylate (18.01 g, 86.5 mmol) in anhydrous acetonitrile (1.0 L). Sodium hydride (60% dispersion in oil, 4.15 g, 104 mmol) was added to the suspension in one portion under nitrogen. The reaction was stirred at room temperature for 2 h. The resulting white suspension was then cooled in an ice bath and iodoacetamide (31.95 g, 173 mmol) was added. The ice bath was then removed and the mixture was stirred 18 h at room temperature. The mixture was quenched with water (50 mL) and the solvent was removed under reduced pressure. The residue was partitioned between diluted NaCl (50 mL brine and 100 mL water) and 1.0 L EtOAc. The aqueous layer was extracted with 2 1.0L EtOAc. The organic layers were combined and dried over Na2S04 and solvent was evaporated under reduced pressure. Crude material was purified on silica gel eluting with 20-50%EtOAc/CH2Cl2 to wash out excess iodoacetamide, and then with 2- 10%MeOH CH2Cl2 to afford a mixture of the two products which were separated on a chiral AD column by eluting with 30% MeOH/C02 to afford the title compound (less mobile fraction). LC- MS – 267.32 [M+l].

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WILKENING, Robert, R.; APGAR, James, M.; BIFTU, Tesfaye; FENG, Danqing; QIAN, Xiaoxia; WEI, Lan; WO2011/103256; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics