Day: July 13, 2021

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 138786-86-4 as follows. Application In Synthesis of Methyl 4-nitro-1H-pyrazole-3-carboxylate

Preparation of tert-Butyl (3-Amino-1-phenyl-1H-pyrazol-4-yl)carbamate (I); A solution of methyl 4-nitro-1H-pyrazole-3-carboxylate (54.0 g, 315.6 mmol), phenylboronic acid (77.0 g, 631.2 mmol), copper(II) acetate (86.0 g, 473.4 mmol) and pyridine (49.9 g, 631.2 mmol) in methylene chloride (600 mL) was stirred at ambient temperature open to air for 48 hours. The reaction was evaporated in vacuo, diluted with 1000 mL methylene chloride and filtered through a large plug of silica (washing with 2 liters methylene chloride). The solvent was evaporated in vacuo. 1H NMR (CDCl3) delta 8.61 (s, 1H), 7.73 (m, 2H), 7.50 (m, 3H), 4.02 (s, 3H).

According to the analysis of related databases, 138786-86-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Berk, Scott C.; Close, Joshua; Hamblett, Christopher; Heidebrecht, Richard W.; Kattar, Solomon D.; Kliman, Laura T.; Mampreian, Dawn M.; Methot, Joey L.; Miller, Thomas; Sloman, David L.; Stanton, Matthew G.; Tempest, Paul; Zabierek, Anna A.; US2007/117824; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1001020-14-9,Some common heterocyclic compound, 1001020-14-9, name is 3-(Trifluoromethyl)-1H-pyrazole-4-carbaldehyde, molecular formula is C5H3F3N2O, 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.

e) 2-(2-(4-Formyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl)acetamido)-N-(2-hydroxyethyl)- 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide2-(2-Bromoacetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3- carboxamide (2.91 g, 8.06 mmol) was dissolved in DMF (25 ml.) and potassium carbonate (2.23 g, 16.11 mmol), followed by 3-(trifluoromethyl)-1 H-pyrazole-4-carbaldehyde (1.39 g, 8.46 mmol), added. The mixture was stirred at 60 0C for 25 min after which time the reaction mixture was diluted with water (-800 ml_), then acidified with 5 N HCI until pH 1. During acidification a free flowing solid was obtained which was collected by filtration. NMR analysis indicated ~60-70 % purity of desired product. The solid was succesfully triturated with a mixture of DCM/ether to give a light beige solid which was collected by filtration. The mother liquor was concentrated and a second batch obtained using a similar process. The batches were combined to yield the title product (1.76 g, 3.95 mmol, 49 %). MS (ESI) : m/z 443.5 [M – H]

The synthetic route of 1001020-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2008/3452; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 89501-90-6, 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 89501-90-6 as follows.

EXAMPLE 5 1-Methylpyrazole-3-sulfonamide A mixture containing chloroform (100 ml), 13.6 g of 1-methylpyrazole-3-sulfonyl chloride and 13.6 g ammonium carbonate was heated to reflux for six hours, cooled, filtered and the solid was washed with water. The water-insoluble solid which was recrystallized from 50% ethanol-water melted at 149-151 and showed absorption peaks in the infrared at 3100 and 3200 cm-1, consistent for the NH2 in the desired product. Anal. Calc. for C4 H7 N3 O2 S: C, 29.8; H, 4.38; N, 26.07; S, 19.9. Found: C, 29.3; H, 4.6; N, 25.3; S, 19.2.

According to the analysis of related databases, 89501-90-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4931081; (1990); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 930-36-9, name is 1-Methylpyrazole, 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 930-36-9, SDS of cas: 930-36-9

The N-methylpyrazole sulfonyl chloride was prepared by adding N- methylpyrazole to chilled (0C) chlorosulfonic acid. The reaction mixture was allowed to warm to room temperature and then heated to 100C overnight under a stream of N2. The reaction mixture was then cooled to room temperature and chilled to 0C. To this solution was added thionyl chloride (2.5 eq. ) and the reaction was stirred at room temperature for 30 min. , then warmed to 70C for two hours. The reaction was cooled to room temperature and then chilled in an ice bath. Water and ice were slowly added to the reaction mixture to precipitate a white solid which was collected by filtration. The desired sulfonyl chloride was washed with cold water and hexane.

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

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/97162; (2005); 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. 67-51-6, name is 3,5-Dimethyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H8N2

(1000mg, 10.40mmol) and KOH (1675mg, 10.40mmol) was dissolved in DMSO, and the resulting heterogeneous solution was stirred at 80 1.5h, then cooled to room temperature. Then, added over 15 minutes a solution of 6M DMSO (876mg, 15.61mmol), and the reaction mixture was stirred for 2.5 hours. TLC observation to monitor whether the reaction is complete. The reaction was dissolved in water, the aqueous phase with CHCl3 extraction. The combined organic layers were washed with 100ml of water, dried over anhydrous Na2SO4, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with 20% ethyl acetate in petroleum ether. To give a yellow oil.

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 67-51-6.

Reference:
Patent; Southern Medical University; Cheng Kui; Xu Yao; (20 pag.)CN109867662; (2019); A;,
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. 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 3994-50-1

To tert-butyl N-[( iS)- 1 -(3 -bromo-5 -fluorophenyl)but-3 -en-i -yl] carbamate (0.19 g, 0.552 mmol), i-methyl-4-nitro-iH-pyrazole (0.070 g, 0.552 mmol), di(adamantan-i20 yl)(butyl)phosphine (0.059 g, 0.166 mmol), pivalic acid (0.019 ml, 0.166 mmol), K2C03(0.229 g, 1.656 mmol) was added DMF (1.1 ml), and the mixture was purged with Ar. Pd(OAc)2 (0.025 g, 0.110 mmol) was added and the reaction was heated at 120 C for 18 h. The reaction was partitioned between water (15 ml) and EtOAc (30 ml). The aqueous layer was extracted with EtOAc (2 x 20 ml). The combined organic layers was washedwith brine (15 ml), dried over MgSO4, filtered and concentrated. The residue was purified by normal phase chromatography using hexanes and EtOAc as eluents to give tert-butyl N- [(15)-i -[3 -fluoro-5 -(1 -methyl-4-nitro- iH-pyrazol-5 -yl)phenyl]but-3 -en-i -yl]carbamate (0.123 g, 57%) as a yellow oil. ?HNMR(400MHz, CDC13)oe 8.23- 8.i7(m, iH), 7.22-7.16 (m, 1H), 7.10 (s, 1H), 7.01 (dt,J=8.5, 1.9 Hz, 1H), 5.76-5.60 (m, 1H), 5.22-5.11(m, 2H), 4.90 (br. s., 1H), 4.78 (br. s., 1H), 3.78 – 3.69 (m, 3H), 2.60 – 2.48 (m, 2H), 1.41(br. s., 9H).

According to the analysis of related databases, 3994-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (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. 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., SDS of cas: 285984-25-0

A heterogeneous mixture of a solution of Na2C03 (3.84 g, 36 mmol) in water (42 mL) and Intermediate A (10.5 g, 45.7 mmol) in isopropyl acetate (130 mL, 1 .082 mol) was stirred vigorously at RT for 5 min and was then treated with phenyl carbonochloridate (5.77 mL, 45.7 mmol). Stirring of the mixture was continued for a further 4 hr after which the layers were separated. The organic phase was added to a solution of Intermediate C (10.0 g, 30.5 mmol) and triethylamine (423 mu?, 3.05 mmol) in isopropyl acetate (60 mL, 51 1 mmol). The reaction mixture was warmed to 48 C for 1 hr, then diluted with isopropyl acetate (190 mL) and cooled to RT for a further 18 hr, during which time a precipitate formed. The precipitate was isolated by filtration, washed with isopropyl acetate and then dried in vacuo at 40 C to afford the title compound, Compound (1 ) as a white solid (anhydrous free base, polymorphic form A) (16.5 g, 92 %); R’ 2.74 min (Method 2); m/z 584 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-de) delta: 1.30 (9H, s), 2.41 (3H, s), 6.43 (1 H, s), 6.58 (1 H, d), 6.78 (1 H, t), 6.97 (2H, t), 7.28 (2H, br m), 7.39 (2H, d), 7.40 (1 H, d), 7.49 (2H, d), 7.56 (1 H, m), 7.63 (1 H, m), 7.82 (1 H, dd), 7.95 (1 H, d), 8.10 (1 H, d), 8.40 (1 H, d), 8.77 (1 H, s), 9.16 (1 H, br s), 9.50 (1 H, br s).

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; RESPIVERT LIMITED; ITO, Kazuhiro; CHARRON, Catherine Elisabeth; KING-UNDERWOOD, John; ONIONS, Stuart Thomas; LONGSHAW, Alistair Ian; BROECKX, Rudy; FILLIERS, Walter; COPMANS, Alex; WO2013/50757; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 35344-95-7,Some common heterocyclic compound, 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 solution of lH-pyrazole-4-carbaldehyde (500 mg, 5.20 mmol) in DMF (20 mL) was added l-bromo-2-methoxyethane (713 mg, 5.2 mmol) and CS2CO3 (3.40 g, 10.4 mmol). After stirring at 60 C overnight, water (20 mL) was added to the mixture and the mixture was extracted with EtOAc (50 ml x 3). The organic phase was washed with brine, dried over Na2S04 and concentrated to yield intermediate 50 (520 mg, 65%> yield).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PATRICK, Aaron Nathaniel; (161 pag.)WO2018/50684; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5334-40-7, These common heterocyclic compound, 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, 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 solution of EDC (4.81 g 25 mmol), HOBt (3.40 g, 25 mmol) and triethylamine (4.67 g, 46 mmol) in DMF (100 ml) was added 4-nitro-lH-pyrazole-3-carboxylic acid (3.63 g, 23.09 mmol) and 4,5-dimethoxy-benzene-l,2-diamine dihydrochloride (5.06g, 20.99 mmol) and the mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the resulting solid partitioned between EtOAc (50 ml) and saturated aqueous NaHCO3 (50 ml). A precipitate was formed and removed by filtration. The filtrate was washed with water followed by diethyl ether and then azeotroped with MeOH and toluene to yield 4- nitro-lH-pyrazole-3- carboxylic acid (2-amino-4,5-dimethoxy-phenyl)- amide (2.35 g, 36percent). 4-Nitro- lH-pyrazole-3-carboxylic acid (2-amino-4,5-dimethoxy-phenyl)-amide (2.35g, 7.65 mmol) was dissolved in acetic acid (150 ml) and refluxed at 140° C for 5 hours. The solution was left to cool and the solvent removed in vacuo. The resulting solid was partitioned between EtOAc (25 ml) and brine (25 ml). The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo to yield 5,6- dimethoxy-2-(4-nitro-lH-pyrazol-3-yl)-lH-benzimidazol (2.08 g, 94percent).

The synthetic route of 5334-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/70195; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 146941-72-2, 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. 146941-72-2, name is 4-Bromo-1-methyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of N-(2′,4′-difluoro-5-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-1-yl)-[1,1′-biphenyl]-3-yl)cyclopropanesulfonamide (100 mg, 0.181 mmol) in THF/EtOH/Water (5:5:2) was degassed by N2 bubbling for 5 min. 4-Bromo-1-methyl-1H-pyrazol-3-amine (35 mg, 0.19 mmol, 1.1 eq.) was added and the mixture was degassed for another 5 min. Bis(tri-tert-butylphosphine)palladium(0) (5 mg, 0.009 mmol, 0.05 eq.) and cesium carbonate (170 mg, 0.54 mmol, 3.0 eq.) were added sequentially and the mixture was further degassed for 5 min and heated at 90 C. for 16 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to give the crude residue which was purified by preparative HPLC to give the product in 27% yield (25 mg). 1H NMR (300 MHz, DMSO): delta 10.3 (s, 1H) 8.79 (s, 1H), 7.95-7.92 (m, 2H), 7.77-7.07 (m, 2H), 7.59 (s, 2H), 7.53-7.47 (m, 3H), 7.29 (m, 1H), 3.75 (s, 3H), 2.91 (m, 1H), 1.5-1.49 (d, 2H), 1.30-1.26 (t, 2H), 1.03-1.01 (t, 2H); LC-MS (ESI): Calculated mass: 520.5; Observed mass: 521.0 [M+H]+ (rt: 0.676 min).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-1-methyl-1H-pyrazol-3-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Linnanen, Tero; Wohlfahrt, Gerd; Nanduri, Srinivas; Ujjinamatada, Ravi; Rajagopalan, Srinivasan; Mukherjee, Subhendu; US2015/11548; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics