Day: May 21, 2021

Electric Literature of 107862-65-7, The chemical industry reduces the impact on the environment during synthesis 107862-65-7, name is 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole, I believe this compound will play a more active role in future production and life.

Step 8: Bromine (22.4 mL, 435 mmol) was added to a solution of 5,6-dihydro-4H- pyrrolo[l,2-b]pyrazole 8 (47.2 g, 437 mmol) and NaOAc (36.2 g, 440 mmol) in AcOH (750 mL) o drop wise at 0 C. The mixture was stirred at the same temperature for 10 minutes then neutralized by the addition of aqueous sodium bicarbonate. The aqueous layer was extracted with EtOAc (5 x 200 mL) and the organic extracts were dried over magnesium sulfate and concentrated under reduced pressure to afford 3-bromo-5,6-dihydro-4H-pyrrolo[l,2-b]pyrazole (73.5 g).

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, 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michele, R.; ALTMAN, Michael, D.; ROMEO, Eric, T.; VITHARANA, Dilrukshi; CASH, Brandon; SIU, Tony; ZHOU, Hua; CHRISTOPHER, Matthew; KATTAR, Solomon, D.; HAIDLE, Andrew, M.; CHILDERS, Kaleen Konrad; MADDESS, Matthew, L.; REUTERSHAN, Michael, H.; DUCHARME, Yves; GUERIN, David. J.; SPENCER, Kerrie; BEAULIEU, Christian; TRUONG, Vouy Linh; GUAY, Daniel; NORTHRUP, Alan, B.; TAOKA, Brandon, M.; LIM, Jongwon; FISCHER, Christian; BUTCHER, John, W.; OTTE, Ryan, D.; SUN, Binyuan; WO2013/192125; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 5952-93-2, These common heterocyclic compound, 5952-93-2, name is Methyl 1-methyl-1H-pyrazole-4-carboxylate, 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 stirred solution of LDA (2.0 M in THF) (10.7 mL, 21.42 mmol) in THF (10.0 mL) was added methyl 1-methyl- 1H-pyrazole-4-carboxylate (1.0 g, 7.14 mmol) in THF (10.0 mL) at -78 C slowly and stirred for 2 h. Dimethylformamide (2.5 mL, 32.84 mmol) was added to the reaction mixture at -78C and then allowed to stir at 0 C for 2 h. The reaction mixture was quenched with aqueous 1 M HC1 solution (10 mL) and extracted with EtOAc (3 x 10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Crude product was purified with silica gel chromatography using20% EtOAc / petroleum ether to afford 0.200 g of methyl 5-formyl-i-methyl-1H-pyrazole-4- carboxylate as pale yellow solid.?H NMR (400 MHz, CDC13) oe ppm 3.91 (s, 3H), 4.20 (s, 3H), 7.91 (s, 1H), 10.50 (s, 1H).

The synthetic route of 5952-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORION CORPORATION; HAIKARAINEN, Anssi; KUMPULAINEN, Esa; POHJAKALLIO, Antti; PYSTYNEN, Jarmo; WANG, Shouming; (191 pag.)WO2018/2437; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 128694-63-3, A common heterocyclic compound, 128694-63-3, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, molecular formula is C6H5F3N2O2, 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 81B N-((3S,4R)-1-((8-Chloroquinoxalin-6-yl)carbonyl)-3-phenylpiperidin-4-yl)-1-methyl-3-(trifluoromethyl)-1 H-pyrazole-5-carboxamide To a solution of 1-methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (0.075 g), a 0.24 M solution of ((3S,4R)-4-amino-3-phenylpiperidin-1-yl)(8-chloroquinoxalin-6-yl)methanone in DMF (1.1 mL), HOBt (0.052 g) and triethylamine (0.11 mL) in DMF (1.0 mL), WSC (0.071 mL) was added at room temperature, and the mixture was stirred for 16 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate/THF. The extract was washed with a saturated aqueous solution of potassium carbonate, water and saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to obtain the title compound (0.10 g). 1H NMR (300 MHz, DMSO-d6) delta 1.57-2.12 (2H, m), 3.34-3.48 (1H, m), 3.51-3.83 (2H, m), 3.87 (3H, s), 3.91-4.10 (1H, m), 4.11-4.46 (1H, m), 4.48-4.76 (1H, m), 7.07-7.45 (6H, m), 8.03 (1H, d, J = 9.6 Hz), 8.13 (1H, brs), 8.46 (1H, d, J = 9.0 Hz), 8.99-9.19 (2H, m).

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; ASANO, Yasutomi; KOJIMA, Takuto; KURASAWA, Osamu; WONG, Tzu-Tshin; HIRATA, Yasuhiro; IWAMURA, Naoki; SAITO, Bunnai; TANAKA, Yuta; ARAI Ryosuke; IMAMURA, Shinichi; YONEMORI, Kazuko; MIYAMOTO, Yasufumi; KITAMURA, Shuji; SANO, Osamu; (222 pag.)EP3287441; (2018); 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. 19959-77-4, name is 2-(5-Methyl-1H-pyrazol-3-yl)pyridine, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(5-Methyl-1H-pyrazol-3-yl)pyridine

General procedure: Solid HL (15.9 mg, 0.10 mmol) and CuCl22H2O (16.8 mg,0.10 mmol) were separated into two arms of an H-tube, whichwas filled with ethanol or acetone solution and subsequentlysealed with thin film. Dark blue block crystals of complex 1 wereobtained after two weeks. The crystals were washed with n-hexane2 3 times, then dried in a vacuum.

According to the analysis of related databases, 19959-77-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Feng-Lei; Zhu, Guang-Zhou; Liang, Bei-Bei; Shi, Yan-Hui; Li, Xiu-Ling; Polyhedron; vol. 128; (2017); p. 104 – 111;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 137890-05-2,Some common heterocyclic compound, 137890-05-2, name is 1-(1-Methyl-1H-pyrazol-5-yl)ethanone, molecular formula is C6H8N2O, 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 74 (R)-N-((5)-2-(2,4-difluorophenyl)-4-(l -methyl- lH-pyrazol-5-yl)-4-oxobutan-2-yl)-2- methylpropane-2-sulfinamide A solution of 2.4 M n-butyllithium in hexane (1.933 mL, 4.83 mmol) was added to a solution of 1-(1 -methyl- lH-pyrazol-5-yl)ethanone (600 mg, 4.83 mmol) in THF (20 mL) maintained at -78 C under a nitrogen atmosphere. The resulting mixture was allowed to stir for 20 min at -78 C. A solution of (R,E)-N-(l-(2,4-difluorophenyl)ethylidene)-2- methylpropane-2-sulfinamide (preparation 73, 836 mg, 3.22 mmol) in THF (5 mL) was slowly added over 2 min. After 5 min, the resulting solution was warmed to between -30 and -20 C and allowed to stir for 24 h. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with EtOAc. The combined organics were washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The crude product was purified using silica gel column chromatography (5: 1-1 : 1 hexanes/ethyl acetate, linear gradient) to afford ( ?)-N-((5)-2- (2,4-difluorophenyl)-4-(l -methyl- lH-pyrazol-5-yl)-4-oxobutan-2-yl)-2-methylpropane-2- sulfinamide (330 mg, 0.861 mmol, 27 % yield). MS (M+Na)+: 406.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(1-Methyl-1H-pyrazol-5-yl)ethanone, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WU, Yong-Jin; GUERNON, Jason M.; WO2014/98831; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1245772-13-7,Some common heterocyclic compound, 1245772-13-7, name is Methyl 1-(2,2,2-trifluoroethyl)-1H-pyrazole-3-carboxylate, molecular formula is C7H7F3N2O2, 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 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

Reference of 575452-22-1, 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. 575452-22-1, name is 1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1-(1-etboxyethyl)-4-iodo-IH-pyrazole (84a)(5 g, 18.79 mmol)(Prepared as reported by Lin, Qiyan et al; Organic Leilers I 1(9): 1999-2002 (2009)) in ether (16 mL) cooled to -78C was added dropwise a solution of n-butyllithium (12.0 mL, 19.2rnmol) in hexane followed by stirring for 30 mins at -78 C. To the anion formed was addeda solution of 3-nitrobenzaldehyde (31a) (2.87 g, 18.79 mmol) in THF (24 mL) slowly at -78 C, stirred at -78 C for 2 h and then at room temperature for 2 h. The reaction mixturewas quenched with saturated amnionium chloride (50 m.L). The organic layer was separatedand the aqueous phase was extracted with ethyl acetate (75 mL). The organic layers werecombined washed with brine (60 rnL), dried over MgSO4, filtered and concentrated invacuum. The residue obtained was purified by flash column chromatography [(silica gel 80 g, eluting with hexanes/ethyl acetate (1:0 to 1: 1)] to furnish (I -(I -ethoxyethyl)- I H-pyrazol4-yl)(3-nitrophenyl)methanol (84b) (3.537 g, 64.6%) as a yellow gum; ?H NMR (300 MHz, DMSO-d4) 8.24 (s, I H), 8.11 (ddd, .1 = 8.1, 2.4, 1.1 Hz, I H), 7.82 (ddq, .1 = 7.8, 1.8, 1.0Hz, 1.H), 7.74 (d, .1 0.8 Hz, I H), 7.63 (t, J 7.9 Hz, 1H), 7.37 (s, 1 H), 6.04 (dd, .1 4.8,1.6 Hz, IH), 5.85 (d,.J=4.7 Hz, lH), 5.47 (q,J= 6.0 Hz, IH), 3.43 -3.35 (m, lH). 3.23-3.05 (rn, IH), 1.54 (d, J 6.0 Hz, 3H), 1.00 (td, J = 7.0, 0.6 Hz, 3H); MS (ES+) 314.184M+Na).

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, 1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; WU, Minwan; CHINTAREDDY, Venkat, R.; KUMAR, V., Satish; ZHANG, Weihe; WO2015/134998; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 70817-26-4, These common heterocyclic compound, 70817-26-4, name is (1-Phenyl-1H-pyrazol-4-yl)methanol, 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.

4) Will be 1.74 g (0.01 muM) 1 – phenyl -4 – hydroxymethyl pyrazole, in 100 ml of the single port in the bottle, by adding 35 ml dichloromethane, stirring in ice bath, dripping 1.43 g (0.012 muM) of thionyl chloride, device end gas collecting device, TLC monitoring after the reaction, reducing pressure and solvent, adding (3 × 50 ml) ethyl acetate extraction, the organic phase with saturated salt water 50 ml washing, desolvation residue after column chromatography (eluting agent is ethyl acetate with petroleum ether (reflux 60 – 90 C), the volume ratio of 1:4) shall be 1.55 g brown solid, yield 81.0%.

The synthetic route of 70817-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenyang Sinochem Pesticide Chemical Research And Development Co., Ltd.; Liu Changling; Guan Aiying; Sun Qin; Yang Jinlong; Li Zhinian; Sun Xufeng; Xia Xiaoli; Ma Sen; Yang Fan; (63 pag.)CN107964007; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 52096-24-9, name is 1-Butyl-1H-pyrazole, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 52096-24-9, Product Details of 52096-24-9

Example 164 Preparation of 1-butyl-alpha-phenyl-1H-pyrazole-5-methanol A solution of 12.4 g of 1-butylpyrazole in 100 ml of absolute ether is placed in a three-necked flask provided with a stirrer, a condenser, a dropping adapter and a thermometer, it is cooled with ice and 6.1 g of a 1.6M solution of butyllithium in hexane are added slowly. The mixture is stirred for 30 minutes and a solution of 14.5 g of p-chlorobenzaldehyde in 30 ml of absolute ether is added slowly. After the reaction, stirring is continued until the mixture reaches room temperature, after which it is hydrolyzed with 100 ml of water. Extraction is carried out with benzene, the benzene phase is washed and dried over sodium sulfate and the solvent is removed in vacuo. This gives 18.9 g (82%) of an oil which can be crystallized from a methanol/water mixture to give crystals melting at 46-7 C., the product being 1-butyl-alpha-phenyl -1H-pyrazole-5-methanol.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Laboratorios del Dr. Esteve, S.A.; US5017596; (1991); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 709-04-6, 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. 709-04-6, name is 1-Phenyl-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of nitrile 1011 (6.0 g, 35.5 mrnol) in THF (70 mL) at 0C was addedTi(O-i-Pr)4 (11.09 rnL, 39.05 rnmoi). To the above reaction mixture under argon atmosphere the1M solution of Grignard reag.ent in THF (78.1 mL, 78.1 mmoi) was added dropwise and thereaction mixture was stirred at —78C for 0.5 h. Then the reaction mixture was stirred at 0C for1.5 h. BF3OEt2 (10.0 rnL, 71.1 mrnol) was added to the above reaction mixture which wasstirred for 0.5 h. After completion of the reaction, the reaction mixture was treated with HCI (2N, 30 mL) and stirred for 15 mm and then basified with 6N NaOH. The mixture was extracted with ethyl acetate (3 x 100 mL) and the organic layers dried over anliydrous Na2SO,, and concentrated under reduced pressure. The crude residue was further purified by Combifiash column chromatography (ethyl acetate/hexane, 0 to 100%) to separate racemic 1021 A (1.0 g)(trans) and racernic 102 lB (0.8 g) (cis) oils.MS (MM) m/: 214.1[M±F1]/

The synthetic route of 1-Phenyl-1H-pyrazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IOMET PHARMA LTD.; MERCK SHARP & DOHME CORP.; COWLEY, Phillip, M.; HAN, Yongxin; (67 pag.)WO2017/48612; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics