Day: September 8, 2021

Reference of 5932-27-4, A common heterocyclic compound, 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, molecular formula is C6H8N2O2, 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 2M aqueous sodium hydroxide solution (1.8 mL, 3.6 mmol) was added to a solution of ethyl 1 H-pyrazole-4-carboxylate (0.2g, 1.55 mmol) in ethanol (4 mL). The reaction mixture was stirred at room temperature overnight and at 80 °C for 2 further hours. The ethanol was evaporated and the mixture was neutralized to give a precipitate which was filtered and dried to give the title compound (0.089 g, 51percent) as a white solid.LRMS (m/z): 113 (M+1)+.

The synthetic route of 5932-27-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; BACH TANA, Jordi; PAGES SANTACANA, Lluis Miquel; TALTAVULL MOLL, Joan; CATURLA JAVALOYES, Juan Francisco; MATASSA, Victor Giulio; WO2011/76419; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 4054-67-5,Some common heterocyclic compound, 4054-67-5, name is 3,3′,5,5′-Tetramethyl-1H,1’H-4,4′-bipyrazole, molecular formula is C10H14N4, 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.

The ligands 5-(4-carboxyphenoxy)isophthalicacid (H3L) (0.10 mmol, 0.031 g) and 3,3?,5,5?-tetramethyl-4,4?-bipyrazole(bpz) (0.10 mmol, 0.020 g) as well as Cd(OOCCH3)2·2H2O(0.10 mmol, 0.027 g) were dissolved in 10 mL of H2O and the mixturewas stirred for 30 min and then transferred and sealed in a 25 mLTeflon-lined reactor and heated to 160 C for 72 h, and thereafter cooledto room temperature at a rate of 5 C/h. Yellow block crystals of 1 wereobtained in 62% yield based on cadmium. IR: 3397(v); 2924(m);1615(m); 1557(vs); 1509(m); 1450(s); 1372(vs); 1246(vs); 1108(m);970(m); 779(m); 724(m); 640(m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,3′,5,5′-Tetramethyl-1H,1’H-4,4′-bipyrazole, its application will become more common.

Reference:
Article; Cai, Shu-Lan; Lu, Lu; Wu, Wei-Ping; Wang, Jun; Sun, Yan-Chun; Ma, Ai-Qing; Singh, Amita; Kumar, Abhinav; Inorganica Chimica Acta; vol. 484; (2019); p. 291 – 296;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 100114-57-6, 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. 100114-57-6, name is 3-Cyclopropyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Potassium carbonate (7.67 g, 55.56 mmol) was added to 3-cyclopropyl-1 H-pyrazole (2.0 g, 18.52 mmol) in dry DMF (20 ml_) at 25C and the mixture was stirred for 20 minutes. Ethyl bromoacetate (2.06 ml_, 18.52 mmol) was added then the mixture was stirred for 2 days at room temperature. The reaction mixture was neutralized with aqueous 1 M HCI, extracted with ether (40 ml_) and the organic extract was washed with brine (30 ml_), dried over sodium sulfate then evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with hexane:EtOAc 88:12 to afford the title compound as a yellow oil (42%, 1 .50 g). 1H NMR (400 MHz, DMSO-d6): delta ppm 0.59 (d, 2H), 0.83 (d, 2H), 1 .19 (t, 3H), 1 .83 (m, 1 H), 4.13 (q, 2H), 4.91 (s, 2H), 5.94 (d, 1 H), 7.54 (d, 1 H)

The synthetic route of 3-Cyclopropyl-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; ANDREWS, Mark, David; BAGAL, Sharanjeet, Kaur; BROWN, David, Graham; GIBSON, Karl, Richard; OMOTO, Kiyoyuki; RYCKMANS, Thomas; SABNIS, Yogesh; SKERRATT, Sarah, Elizabeth; STUPPLE, Paul, Anthony; WO2014/53967; (2014); 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 31037-02-2 as follows. COA of Formula: C7H11N3O2

Intermediate 32: Ethyl 5-(benzylsulfanyl)-l-methyl-lH-pyrazole-4-carboxylate Dibenzyl disulfide (101.9 g, 413.57 mmol) was added in portions to a solution of ethyl 5- amino-1 -methyl- lH-pyrazole-4-carboxylate (10 g, 59.11 mmol) in MeCN (400 mL) in an atmosphere of nitrogen and at rt. CuCl (293 mg, 7.14 mmol) was added in portions at rt to the reaction mixture and it was stirred at rt for 30 min. 3 -Methyl- 1-nitrobutane (41.5 g, 354.26 mmol) was added to the reaction mixture and the resulting solution was stirred at rt for 30 min and then at 60C for 1 h. The reaction mixture was allowed to reach rt and the solids were filtered off. The filtrate was concentrated under vacuum and the residue was purified by silica gel column chromatography (EtO Ac/petroleum ether, 1 :8) to give the title compound (11.6 g, 71%) as yellow oil. MS m/z 111 [M+H]+

According to the analysis of related databases, 31037-02-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; BRODDEFALK, Johan, Olof; EMTENAeS, Hans, Fredrik; GRANBERG, Kenneth, Lars; LEMURELL, Malin, Anita; PETTERSEN, Daniel, Tor; PLOWRIGHT, Alleyn, Thomas; ULANDER, Lars, Johan, Andreas; (161 pag.)WO2016/177703; (2016); 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. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

A solution of 3-(4-chloro-2-methylphenyl)piperidine hydrochloride (50 mg, 0.203 mmol) (Intermediate la5) in DCM (10 mL) was treated with 1,3 -dimethyl- lH-pyrazole-4- carboxylic acid (31.3 mg, 0.223 mmol), l-ethyl-3-(3-dimethylaminopropyl)carbodimide hydrochloride (48.7 mg, 0.254 mmol), 1-hydroxybenzotriazole hydrate (34.8 mg, 0.227 mmol) and triethylamine (0.057 mL, 0.406 mmol). The mixture was stirred at room temperature for 17 hours. Water was added to the reaction mixture which was stirred vigorously for 30 minutes before the phases were separated using a phase separation cartridge. The organic phase was concentrated in vacuo. The crude product was purified by preparative LCMS (basic conditions) to give the title compound 3-(4-chloro-2- methylphenyl)-l-[(l,3-dimethyl-lH-pyrazol-4-yl)carbonyl]piperidine (42 mg, 62%). 1H NMR (400 MHz, DCM-d2) delta ppm 1.57 – 2.07 (m, 4 H) 2.32 (s, 6 H) 2.78 – 3.07 (m, 3 H) 3.87 (s, 3 H) 4.12 – 4.52 (m, 2 H) 7.14 – 7.22 (m, 3 H) 7.45 (s, 1 H) MS ES+: 332

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 78703-53-4.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BOUSBA, Sarah; GOLDBY, Anne; JENKINS, Kerry; KINSELLA, Natasha; TEALL, Martin; WO2015/19103; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3463-30-7,Some common heterocyclic compound, 3463-30-7, name is 1-(4-Nitrophenyl)-1H-pyrazole, molecular formula is C9H7N3O2, 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.

[00264] To a stirred solution of compound 2 (2.4 g, 12.7 mmol) in EtOH (20 mL) at RT, was added 10% Pd/C (50% wet, 500 mg). The reaction mixture was stirred at RT under hydrogen (1 atmosphere pressure) for 16 h. The mixture was filtered through a pad of celite and the celite bed was washed with methanol (30 mL). The filtrate was concentrated under reduced pressure to afford compound 3 (1.7 g, 79% over two steps) as colorless oil, which did not require further purification. H MR (400 MHz, DMSO-i: delta 8.18 (d, J = 2.0 Hz, 1H), 7.60 (d, J= 1.4 Hz, 1H), 7.42 (d, J = 8.8 Hz, 2H), 6.63 (d, J= 8.8 Hz, 2H), 6.42 (t, J= 1.9 Hz, 1H), 5.19 (s, 2H).

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

Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; (114 pag.)WO2017/139274; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

82560-12-1,Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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.

A5. General Method for the Synthesis of BOC-Protected Pyrazoles; 5-Amino-3-tert-butyl-N1-(tert-butoxycarbonyl)pyrazole; To a solution of 5-amino-3-tert-butylpyrazole (3.93 g, 28.2 mmol) in CH2Cl2 (140 mL) was added di-tert-butyl dicarbonate (6.22 g, 28.5 mmol) in one portion. The resulting solution was stirred at room temp. for 13 h, then diluted with EtOAc (500 mL). The organic layer was washed with water (2×300 mL), dried (MgSO4) and concentrated under reduced pressure. The solid residue was triturated (100 mL hexane) to give the desired carbamate (6.26 g, 92%); mp 63-64 C.; TLC Rf (5% acetone/95% CH2Cl2); 1H-NMR (DMSO-d6) delta 1.15 (s, 9H), 1.54 (s, 9H), 5.22 (s, 1H), 6.11 (s, 2H); FAB-MS m/z ((M+H)+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-5-tert-butylpyrazole, its application will become more common.

Reference:
Patent; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Paulsen, Holger; Riedl, Bernd; Scott, William J.; Smith, Roger A.; Wood, Jill E.; Hatoum-Mokdad, Holia; Johnson, Jeffrey; Lee, Wendy; Redman, Aniko; Sibley, Robert; Renick, Joel; US2007/244120; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 15754-60-6,Some common heterocyclic compound, 15754-60-6, name is 1-(tert-Butyl)-1H-pyrazole, molecular formula is C7H12N2, 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 suspension of Na2CO3 (3.6 g, 33.9 mmol) in CH2Cl2 (30 mL) was added 1-tert-butyl-1H-pyrazole (2.1 g, 17 mmol) and Br2 (0.9 mL). The mixture was stirred at roomtemperature overnight. The formed solid was removed by filtration and the filter cake waswashed with CH2Cl2 (30 mL). The filtrates were washed with water (20 mL) and brine (20 mL), dried (MgSO4), and concentrated under reduced pressure to afford crude 4-bromo-1-tert-butyl-1H-pyrazole (2.9 g, 85%), which was used in next step without further purification. MS (ESI)m/z: 203 [M+H]+.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; TSUI, Vickie, H.; WANG, Xiaojing; WO2014/1377; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1904-31-0

1 -Methyl- lH-pyrazo 1-3 -amine (158 mg, 1.63 mmol) and DIEA (1.08 mL, 6.52 mmol) was added to a solution of 2-(l-(ter^-butoxycarbonylamino)cyclobutyl)-2-hydroxyacetic acid (400 mg, 1.63 mmol) dissolved in DMF (20 mL). The solution was cooled to 00C and after 10 minutes HATU (620 mg, 1.63 mmol) was added. After approximately 2 hours at RT, LC-MS showed product and no starting material and the solvent was removed by rotary evaporation. The crude product was dissolved in 40 rnL of EtOAc and washed with 25 rnL of sat. NaHCCh (aq). The organic phase was dried with Na2SO4, filtered and evaporated to dryness. The crude product was purified on a 25 g silica column on a Biotage Flashmaster eluted with a gradient of heptane:ethyl acetate 1 :1, which gave the title compound as a white solid (488 mg, 92percent) yield. [M+H]+ = 325.

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR UK LTD; AYESA, Susana; BELFRAGE, Anna, Karin; CLASSON, Bjoern; GRABOWSKA, Urszula; HEWITT, Ellen; IVANOV, Vladimir; Joensson, Daniel; KAHNBERG, Pia; LIND, Peter; NILSSON, Magnus; ODEN, Lourdes; PELCMAN, Mikael; WAeHLING, Horst; WO2010/70615; (2010); 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. 28466-26-4, name is 4-Aminopyrazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Aminopyrazole

Intermediate 25: 1 ,1-Dimethylethyl 6-[(1 /-/-pyrazol-4-ylamino)carbonyl1-3,4-dihydro- 2(1 HVisoalphauinolinecarboxylate; To a solution of 1 H-pyrazol-4-amine (1.87 g, 22.5 mmol), N-(3-dimethylaminopropyl)- N’-ethylcarbodiimide hydrochloride (5.18 g, 27 mmol), 1-hydroxybenzotriazole hydrate (3.65 g, 27 mmol) and triethylamine (6.3 ml_, 45 mmol) in DMF was added 2- {[(I J-dimethylethyOoxylcarbonylJ-i ^^^-tetrahydro-theta-isoquinolinecarboxylic acid (5.62 g, 20.3 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The volatiles were removed under reduced pressure, the residue was dissolved in MeOH and potassium hydroxide (5.04 g, 90 mmol), water (100 ml.) was added and the mixture was heated at 500C for 15 min. The MeOH was evaporated under reduced pressure and the solid which crystallized was filtered and recrystallized from acetonitrile to give the title compound as a solid (3.7 g, 48%). LC/MS: m/z 341 (M-H)+, Rt: 2.80 min.

According to the analysis of related databases, 28466-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/74824; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics