Tag: M.W:100-200

Synthetic Route of 129768-28-1, These common heterocyclic compound, 129768-28-1, name is 5-(Trifluoromethyl)-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.

Example 9. Procedure for the synthesis of 2-(trifluoromethyl)-5-(3-((3- (trifluo (5H)-one (34); Preparation of methyl 3-(trifluoromethyl)-lH-pyrazole-5-carboxylate (32); 3-(Trifluoromethyl)-lH-pyrazole-5-carboxylic acid (31) (1.0 g, 8.33 mmol) was stirred inMeOH (50 mL) at rt. AcCl (1.18 mL, 16.67 mmol) was added dropwise, and the reaction stirred at reflux for 2 hours. The reaction was concentrated in vacuo and partitioned between EtOAc and saturated NaHC03 solution. The organics were dried (Na2S04) and concentrated in vacuo to give methyl 3-(trifluoromethyl)-lH-pyrazole-5-carboxylate (32) (1.0 g, 93%); NMR (300 MHz, CDC13) delta 3.98 (s, 3H), 7.10 (s, 1 H). The product was used without purification.

Statistics shows that 5-(Trifluoromethyl)-1H-pyrazole-3-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 129768-28-1.

Reference:
Patent; ZALICUS PHARMACEUTICALS LTD.; PAJOUHESH, Hassan; HOLLAND, Richard; ZHOU, Yuanxi; ZHU, Yongbao; GRIMWOOD, Michael Edward; CHAHAL, Navjot; WO2012/61926; (2012); 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. 71229-85-1, name is 4-Bromo-1-ethyl-1H-pyrazole, A new synthetic method of this compound is introduced below., name: 4-Bromo-1-ethyl-1H-pyrazole

1003281 To a solution of compound 3 (4.3 g, 20.5 mmol) in toluene (50 mL) were added 4- bromo-1-ethyl-1H-pyrazole 4(4.0 g, 22.8 mmol), potassium phosphate (11.0 g, 51.2 mmol), N,N?-dimethylethylenediamine (722 mg, 8.2 mmol) and Cu(I)I (390 mg, 2.0 mmol) at RT underinert atmosphere. The reaction solution was purged with argon for 15 mm and then sealed the tube. The reaction mixture was heated to 140 C and stirred for 16 h. After completion of the reaction by TLC, the reaction mixture was cooed to RT, diluted with EtOAc (50 mL) and filtered. The filtrate was washed with water (40 mL), brine (40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified (silica gel chromatography; 9% EtOAc/Hexanes) to afford compound 5 (3.9 g, 63%) as a pale brown solid. 1H NMR (400 MHz, CDC13): 7.64 (s, 1H), 7.60 (s, 1H), 7.16 (d, I = 8.4 Hz, 1H), 7.01 (dd, J =8.4, 6.4 Hz, 1H), 6.12 (s, 1H), 4.25 (q, J = 7.2 Hz, 2H), 1.69-1.62 (m, 1H), 1.56 (t, J = 7.2 Hz, 3H), 0.92-0.87 (m, 2H), 0.76-0.72 (m, 2H); LC-MS (ES): 98.6%; m/z 304.3 (M + Hj; (column: X Select C-18, 50 x 3.0 mm, 3.5 tm); RT 4.23 mill; 5 mM NH4OAc: ACN; 0.8 mL/min).

The synthetic route of 71229-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAKEA, INC.; BAIN, Gretchen; EVANS, Jillian Frances; HUTCHINSON, John Howard; LONERGAN, David; (123 pag.)WO2016/191427; (2016); 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. 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-Chloro-1-methyl-4-nitro-1H-pyrazole

Example 64b 3-Fluoro-5-(4-methoxybenzyloxy)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepane To a solution of tert-butyl 3-fluoro-5-(4-methoxybenzyloxy)azepane-1-carboxylate (740 mg, 0.21 mmol) in MeOH (5 mL) was added HCl (4 M in 1,4-dioxane, 5.3 mL, 21 mmol) and the solution was stirred at room temperature for 16 hr. The solvents were removed under reduced pressure and the residue was dissolved in MeOH and loaded onto an SCX column. The column was washed with MeOH and eluted with 7 N ammonia in MeOH. The solvents were removed under reduced pressure to afford a yellow oil. To a solution of this oil in dry DMSO (15 mL) was added potassium fluoride (0.32 g, 8.4 mmol) and 5-chloro-1-methyl-4-nitro-1H-pyrazole (372 mg, 2.31 mmol) and the mixture was heated at 65 C. for 16 hr. After cooling to room temperature, the mixture was diluted with water (300 mL) and extracted with EtOAc (2*50 mL). The combined organic layers were washed with water (3*50 mL) and the solvent was removed under reduced pressure. Purification via silica gel column chromatography (20-100% EtOAc/isohexane) gave 3-fluoro-5-(4-methoxybenzyloxy)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepane as a yellow oil (300 g, 55% over two steps). 1H NMR (400 MHz, CDCl3) delta 7.33-7.23 (m, 3H), 6.89-6.86 (m, 2H), 4.82-4.66 (m, 2H), 4.49-3.93 (m, 1H), 3.81 (s, 3H), 3.30-2.99 (m, 4H), 2.95-2.74 (m, 4H), 2.35-2.03 (m, 2H), 1.98-1.83 (m, 2H).

The synthetic route of 42098-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 578008-32-9, 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 578008-32-9 as follows.

Typical procedure for the Buchwald reaction with terf-butoxycarbonyl protected pyrazole:2-(2-Chloro-4-trifluoromethyl-phenyl)-4-(5-methyl-lH-pyrazol-3-ylamino)-2H- phthalazin- 1 -one4-Bromo-2-(2-cUoro-4-trifluoromethyl-phenyl)-2H-phthalazin-l-one (obtained from the above phthalazine-l,4-dione by bromination with POBr3 in analogy to Method R, as reported above) (0.15g, 0.37mmol), 3-amino-5-methyl-pyrazole-l- carboxylic acid tert-butyl ester (0.08Og, 0.41mmol), Cs2CO3 (0.033g, 0.34mmol), tris-(dibenzylideneacetone)-dipalladium (0.017g, 0.019mmol) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.022g, 0.037mmol) in 2 ml dry dioxane under nitrogen were heated to 100C for 18 hours, and then allowed to cool to room temperature. H2O was added and the solvent was evaporated in vacuum. The resulting solid was collected by filtration. Purification of the raw product by preparative HPLC gave the title compound (0.069g, 44% yield). 1H- EPO NMR: (400 MHz, D6-DMSO) 11.92 (IH, s), 9.34 (IH, s), 8.54 (IH, d), 8.35 (IH, d), 8.14 (IH, s), 8.01 (IH, t), 7.92 (3H, m), 6.06 (IH, s), 2.14 (3H, s); MS (ESI+) = 420.23 (M+H)+.

According to the analysis of related databases, 578008-32-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2006/32518; (2006); 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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., name: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

A solution of 293 g of 3-difluoromethyl-1-methylpyrazole-4-carboxylic acid, prepared analogously to example 2, in 700 g of toluene was heated at 90 C., and 260 g of thionyl chloride were added over a period of 3.5 h. The mixture was allowed to cool and concentrated under reduced pressure, 100 ml of toluene were added to the residue and the mixture was again concentrated under reduced pressure. The residue was distilled over a packed column at a pressure of 0.8 mbar and a head temperature of 109 C., which gave 298.4 g of the acid chloride of a purity of 99% (yield 92.1%).

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; BASF SE; US2010/69646; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, molecular formula is C4H5BrN2, 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. Computed Properties of C4H5BrN2

10330] To a suspension of NaH 60% in oil (0.3 g; 7.45 mmol) in tetrahydrofuran (150 mE) there is added, at 100 C., 4-bromo-3-methyl-1H-pyrazole dissolved in 15 mE of tetrahydrofuran dropwise, over 15 minutes. Afier stirring for 40 minutes at ambient temperature, iodomethane (0.45 mE; 7.45 mmol) is added dropwise, and then the reaction mixture is stirred overnight. Afier adding water, the reaction mixture is evaporated and taken up in dichloromethane. The organic phase is separated off and dried over Mg504, filtered and concentrated to dryness. The residue is purified by chromatography over silica gel to yield a mixture of the title compounds (4-bromo-1 ,3-dimethyl-pyrazole and 4-bromo-1 ,5- dimethyl-pyrazole respectively in a ratio of 4:6).4-bromo-1 ,5-dimethyl-1H-pyrazole10331] ?H NMR (500 MHz, dmso-d6) oe ppm: 7.41 (s, 1H),3.76 (s, 3H), 2.22 (s, 3H)4-bromo-1 ,3-dimethyl-1H-pyrazole10332] ?H NMR (500 MHz, dmso-d6) oe ppm: 7.81 (s, 1H),3.74 (s, 3H), 2.09 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13808-64-5, its application will become more common.

Reference:
Patent; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; STARCK, Jerome-Benoit; HENLIN, Jean-Michel; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; GENESTE, Olivier; FEJES, Imre; TATAI, Janos; NYERGES, Miklos; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; DURAND, Didier; US2015/31673; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 42027-81-6, 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. 42027-81-6 name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, 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.

Synthesis of compound 22.2. A 50-mL round-bottom flask, was charged with compound 21.1 (100 mg, 0.64 mmol, 1.00 equiv), methanol (5 mL) and palladium on carbon (20 mg). Resulting solution was stirred under H2 gas atmosphere for 1 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum to furnish 70 mg (87%) of compound 22.2 as off-white oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; SHELLEY, Mee; MASSE, Craig E.; HARRIMAN, Geraldine C.; WO2015/164374; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1310350-99-2, A common heterocyclic compound, 1310350-99-2, name is 4-Chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid, molecular formula is C5H3ClF2N2O2, 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.

d) 4-Chloro-l-difluoromethyl-lH-pyrazole-3-carboxylic acid methoxy-methyl-amideF A solution of 4-chloro-l-difluoromethyl-lH-pyrazole-3-carboxylic acid (150 mg, 0.76 mmole) in dichloromethane (5 ml) was subsequently treated at 23 C with N,0- dimethylhydroxylamine hydrochloride (78 mg, 0.80 mmole), N-methylmorpholine (0.09 ml, 0.8 mmole) and EDCI.HC1 (154 mg, 0.8 mmole) and stirring was continued for 16 h. The mixture was washed with 1 M aqueous HCl and H20, the organic layer was dried, evaporated and the residue purified by chromatography on silica gel using cyclohexane/AcOEt (2: 1) to give the title compound (164 mg) as a colorless oil. MS: m/z = 240.1 [M]+.

The synthetic route of 1310350-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A; GABELLIERI, Emanuele; GUBA, Wolfgang; HILPERT, Hans; MAUSER, Harald; MAYWEG, Alexander V.; ROGERS-EVANS, Mark; ROMBACH, Didier; THOMAS, Andrew; WOLTERING, Thomas; WOSTL, Wolfgang; WO2012/126791; (2012); 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. 18213-75-7, name is 5-Amino-1-methyl-1H-pyrazole-4-carboxamide, A new synthetic method of this compound is introduced below., Formula: C5H8N4O

The mixture of 5-amino-1-methyl-1H-pyrazole-4-carboxamide (70 g, 0.49 mol), EtONa (117 g, 1.72 mol) and the intermediate from Step B ( (272 g, 1.16 mol) in EtOH (1 L) was stirred in a sealed bottle at 120C overnight. The mixture was concentrated and the residue was diluted with H2O (2 L) and then adjusted to pH = 6 with 2 N aqueous HC1 solution. The mixture was extracted with EtOAc (1 L x 3). The combined organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography using petroleum ether/EtOAc = 1 : 1 to give the title product.

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; MERCK SHARP & DOHME CORP.; HAN, Xiaoqing; WHITEHEAD, Alan; RAGHAVAN, Subharekha; CERNAK, Timothy, A.; DREHER, Spencer; GROEPER, Jonathan; GUO, Jian; ZHANG, Yong; WO2015/88886; (2015); 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. 13808-64-5, name is 4-Bromo-3-methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C4H5BrN2

Step A: N-Boc-4-bromo-3-methyl-pyrazole. To 4-bromo-3-methyl-pyrazole (3.50 g, 21.7 mmol) was added CH2Cl2 (30 mL), di-tert-butyl dicarbonate (5.22 g, 23.9 mmol) and aq Na2CO3 (1 M, 43.5 mL). The reaction was stirred for 2.5 h and the aq portion was then separated. The CH2Cl2 portion was then washed with 5% citric acid followed by brine/saturated aq NaHCO3 (1:1). The solution was dried (Na2SO4), filtered and concentrated to afford the product.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Clements, Matthew J.; Debenham, John S.; Hale, Jeffrey J.; Madsen-Duggan, Christina B.; Walsh, Thomas F.; Peresypkin, Andrey V.; Helmy, Roy; US2008/269279; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics