Day: June 1, 2021

Adding a certain compound to certain chemical reactions, such as: 3920-50-1, name is Pyrazole-3-carboxaldehyde, 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 3920-50-1, Product Details of 3920-50-1

2-(Trimethylsilyl)ethoxymethyl chloride (14 ml, 78 mmol) was added portionwise over 10 minutes, at -40° C., to a solution of pyrazole-3-carboxaldehyde (5 g, 52 mmol) and diisopropylethylamine (13.6 ml, 78 mmol), in dichloromethane (100 ml). The reaction mixture was then warmed to room temperature and stirred for a further 18 hours, after which time it was quenched with brine and extracted with dichloromethane. The organic layer was separated, dried over magnesium sulphate and concentrated under reduced pressure to provide the crude product (14.6 g). A portion of this (3 g) was purified by flash chromatography on silica gel eluting with ethyl acetate:pentane (5:95 to 10:90 to 20:80, by volume) to provide the title compound (14.6 g, 100percent) as a 1.1:1 mixture of regioisomers. 1H-NMR (400 MHz, CDCl3): 5-0.05 (s, 9H, regioisomer B), -0.02 (s, 9H, regioisomer A), 0.87-0.94 (m, 2HA+2HB), 3.58 (t, 2HA+2HB), 5.51 (s, 2H, A), 5.81 (s, 2H, B), 6.87 (s, 1H, A), 6.97 (s, 1H, B), 7.62 (m, 1 HA+1 HB), 9.95 (s, 1H, B), 10.01 (s, 1H, A); LC-MS: ESI+: m/z 227 [MH+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Pyrazole-3-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Bradley, Paul Anthony; Dack, Kevin Neil; Marsh, Ian Roger; US2006/241125; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application 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

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., Product Details of 78703-53-4

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

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. 133228-21-4, name is N,N-Dimethyl-1H-pyrazole-1-sulfonamide, A new synthetic method of this compound is introduced below., Product Details of 133228-21-4

To a solution of [N-DIMETHYLSULFAMOYLPYRAZOLE] (44.0 g, 0.251 mol) in dry tetrahydrofuran (500 mL) at-78 C was added dropwise a solution of n-butyllithium (2.5 M in hexane, 105.5 mL, 0.264 mol) while maintaining the temperature [BELOW-60 C.] A thick solid formed during the addition. Upon completion of the addition the reaction mixture was maintained for an additional 15 minutes, after which time a solution of 1,2-dibromo- tetrachloroethane (90 g, 0.276 mol) in tetrahydrofuran (150 mL) was added dropwise while maintaining the temperature [BELOW-70 C.] The reaction mixture turned a clear orange; stirring was continued for an additional 15 minutes. The-78 [C] bath was removed and the reaction was quenched with water (600 mL). The reaction mixture was extracted with dichloromethane [(4X)] and the organic extracts were dried over magnesium sulfate and concentrated. The crude product was further purified by chromatography on silica gel using dichloromethane-hexane (50: 50) as eluent to afford the title product as a clear colorless oil (57.04 [G).] 1H NMR [(CDC13)] 8 3.07 (d, 6H), 6.44 (m, 1H), 7.62 (m, 1H).

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; E.I. DU PONT DE NEMOURS AND COMPANY; WO2004/11447; (2004); 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. 28466-26-4, name is 4-Aminopyrazole, This compound has unique chemical properties. The synthetic route is as follows., Safety 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

Electric Literature of 3469-69-0,Some common heterocyclic compound, 3469-69-0, name is 4-Iodopyrazole, molecular formula is C3H3IN2, 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-Iodopyrazole (2.5 g, 1 equiv.) was dissolved in dry DMF (20 mL), and TEA (1.8 mL, 1 equiv.) was added at 0 C. Then, trityl chloride (3.56 g, 0.99 equiv.) was added, and the reaction mixture was stirred at 0 C to RT overnight. The mixture was then poured into ice water (250 mL) and was filtered. The obtained solid was washed with water (150 mL), and was then triturated with toluene (20 mL) and dried under vacuum to afford the expected product (3.48 g), which was used in the next reaction step without further purification.

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

Reference:
Patent; E-THERAPEUTICS PLC; JURKOVIC, Mihaela; LANDEK, Ivana Ozimec; POLJAK, Tanja; RO?CIC, Maja; STUBBERFIELD, Colin; VADLAMUDI, Srinivasamurthy; (228 pag.)WO2019/43372; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature 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

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

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. 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 82560-12-1

3-Tert-butyl-1H-pyrazol-5-amine (J-III) (1 eq., 40 g) was dissolved in dilute HCI (120 ml of HCI in 120 ml of water) and mixed dropwise with NaNO2 (1.03 eq., 25 g in 100 ml) at 0 – 5 0C over a period of 30 min. After stirring for 30 minutes, the reaction mixture was neutralised with Na2CO3. A diazonium salt obtained by reaction of KCN (2.4 eq., 48 g), water (120 ml) and CuCN (1.12 eq., 31 g) was added dropwise to the reaction mixture within 30 min and the mixture was stirred for a further 30 min at 75 0C. After complete reaction, the reaction mixture was extracted with EE (3 x 500 ml), the combined organic phases were dried over sodium sulphate and the solvent was removed under vacuum. The purification (SiO2, 20 % EE/hexane) of the residue by column chromatography produced a white solid (J-IV) (6.5 g, 15.1 % yield).

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; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; SCHIENE, Klaus; DE VRY, Jean; DAMANN, Nils; FRORMANN, Sven; LESCH, Bernhard; LEE, Jeewoo; KIM, Yong-Soo; KIM, Myeong-Seop; WO2010/127855; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 7119-95-1, A common heterocyclic compound, 7119-95-1, name is 1-Nitropyrazole, molecular formula is C3H3N3O2, 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.

N-nitropyrazole is dissolved in benzonitrile, heated to 180 ° C, incubated for 3.5 h,cooled to 50-60 ° C after completion of thereaction, and added to n-hexane to make 3-nitrate The pyrazole is precipitated, filtered and dried to give 3-nitropyrazole;

The synthetic route of 7119-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Science and Technology; Li Bindong; Zhu Xiang; (12 pag.)CN108570010; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics