Tag: M.W:100-200

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. 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

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

Adding a certain compound to certain chemical reactions, such as: 313735-62-5, name is 4-Bromo-1-isopropylpyrazole, 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 313735-62-5, COA of Formula: C6H9BrN2

n–Butyllithium (2.5M in hexanes, 1.38 mL, 3.45 mmol) was added over 15 min to a solution of 4-bromo-1-isopropyl-1H-pyrazole (500 mg, 2.65 mmol) in diethyl ether (10 mL) at -78 C. After 30 min, a solution of tri-n-butylstannane chloride (920 muL, 3.45 mmol) in diethyl ether (1 mL) was added and the resultant reaction mixture was left to stir at -78 C for 1 h, then allowed to warm to ambient temperature. The reaction mixture was diluted with diethyl ether (40 mL) and washed with water (20 mL), then brine (20 mL). The organic layer was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford the title product as a colourless oil (98 mg, 94%) which was used without further purification. 1H-NMR (CDCl3, 400MHz): 7.46- 7.42 (m, 1 H); 7.28 (t, J = 4.2Hz, 1 H); 4.59-4.43 (m, 1 H); 1.58-1.42 (m, 12 H); 1.39-1.24 (m, 6 H); 1.02-0.77 (m, 15 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-isopropylpyrazole, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; WO2009/151598; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 288148-34-5,Some common heterocyclic compound, 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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.

General procedure: A mixture of the appropriate (aryloxy)ethyl piperidine(0.38 mmol) in CH2Cl2 (3 mL), and TEA (1.14 mmol) was cooled down (ice bath), and arylsulfonyl chloride (0.46 mmol) was added at 0 C in one portion. The reaction mixture was stirred for 2-6 h under cooling. Then, the solvent was evaporated and the sulfonamides were purified using silica gel column with CH2Cl2/MeOH as an eluting system. Free bases were then converted into the hydrochloride salts by treatment of their solution in anhydrous ethanol with 1.25 M HCl in MeOH.; 9.2.6.4 1-Methyl-N-(1-{2-[(propan-2-yl)phenoxy]ethyl}piperidin-4-yl}-N-methyl-1H-pyrazole-4-sulfonamide (13) Yellow oil, 90 mg following chromatographic purification over silica gel with CH2Cl2/MeOH (9:0.7); LC/MS purity 96%, tR = 4.47, C21H32N4O3S, MW 420.57, Monoisotopic Mass 420.22, [M+H]+ 421.3 1H NMR (300 MHz, CDCl3) delta 1.19 (d, J = 6.92 Hz, 6H), 1.49-1.58 (m, 2H), 1.71 (qd, J = 12.21, 3.88 Hz, 2H), 2.22 (td, J = 11.89, 2.24 Hz, 2H), 2.73 (s, 3H), 2.81 (t, J = 5.72 Hz, 2H), 2.99-3.07 (m, 2H), 3.29 (quin, J = 6.92 Hz, 1H), 3.81 (tt, J = 11.97, 4.22 Hz, 1H), 3.92 (s, 3H), 4.06 (t, J = 5.72 Hz, 2H), 6.80 (dd, J = 8.14, 0.99 Hz, 1H), 6.88-6.94 (m, 1H), 7.12 (td, J = 7.76, 1.73 Hz, 1H), 7.20 (dd, J = 7.53, 1.67 Hz, 1H), 7.70 (d, J = 0.61 Hz, 1H), 7.74 (s, 1H). 13C NMR (75 MHz, CDCl3) delta 22.70, 26.73, 28.60, 29.27, 39.55, 53.47, 55.03, 57.13, 66.40, 111.26, 120.78, 122.21, 126.06, 126.53, 131.37, 137.03, 138.15, 155.79.

The synthetic route of 288148-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Canale, Vittorio; Kurczab, Rafa?; Partyka, Anna; Sata?a, Grzegorz; S?oczy?ska, Karolina; Kos, Tomasz; Jastrz?bska-Wi?sek, Magdalena; Siwek, Agata; P?kala, Elzbieta; Bojarski, Andrzej J.; Weso?owska, Anna; Popik, Piotr; Zajdel, Pawe?; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 130 – 139;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 119083-00-0, A common heterocyclic compound, 119083-00-0, name is 1-Methyl-5-(trifluoromethyl)-1H-pyrazole-4-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 159 N-(4-{trans-2-[(cyclopropylmethyl)amino]cyclopropyl}phenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide hydrochloride By a method similar to Example 80, the title compound (56.1 mg) was obtained from tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate (82.8 mg) and 1-methyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (63.8 mg). MS (API+): [M+H]+ 379.3. 1H NMR (300 MHz, DMSO-d6) delta 0.29-0.40 (2H, m), 0.52-0.62 (2H, m), 0.95-1.11 (1H, m), 1.18-1.30 (1H, m), 1.39-1.52 (1H, m), 2.32-2.47 (1H, m), 2.82-3.02 (3H, m), 3.98 (3H, s), 7.14 (2H, d, J = 8.6 Hz), 7.61 (2H, d, J = 8.6 Hz), 8.54 (1H, s), 9.01 (2H, brs), 10.12 (1H, s).

The synthetic route of 119083-00-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; TOMITA, Naoki; KAJII, Shigeo; CARY, Douglas Robert; TOMITA, Daisuke; IMAMURA, Shinichi; TSUCHIDA, Ken; MATSUDA, Satoru; HARA, Ryujiro; EP2743256; (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 78703-53-4 as follows. Recommanded Product: 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

1,3-Dimethyl-1H-pyrazole-4-carboxylic acid of formula (III) (7.76 g, 40 mmol)Reflowed with thionyl chloride (47.6 g, 0.4 mol) for 4 hours.When the reaction system turns into a pale yellow transparent liquid,Continue to react for 30 minutes,The reaction stops,After cooling to room temperature, it was distilled under reduced pressure.1,3-dimethyl-1H-pyrazole-4-yl chloride,1,3-Dimethyl-1H-pyrazole-4-yl chloride (2mmol)Add 15ml of dichloromethane,Join(R)-1-phenethyl-1-amine(2.1mmol),Then triethylamine (0.3 g, 3 mmol) was slowly added dropwise at room temperature overnight;TLC (EA: PE=2:1(V)) tracking,After the reaction was completed, it was extracted three times with a dichloromethane/water = 1:1 (V) system.Concentrated organic layer,Extracted with toluene or 75% ethanol,Column chromatography (EA: PE = 2:1 (V)),Obtained (K19)(R)-1,3-dimethyl-N-(1-phenethyl)-1H-pyrazole-4-carboxamide;

According to the analysis of related databases, 78703-53-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang University of Technology; Jin Tao; Wang Han; Tan Chengxia; Weng Jianquan; Han Liang; Liu Xinghai; (9 pag.)CN109156471; (2019); A;,
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. 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Methyl-1H-pyrazole-4-sulfonyl chloride

General procedure: A mixture of the appropriate (aryloxy)ethyl piperidine(0.38 mmol) in CH2Cl2 (3 mL), and TEA (1.14 mmol) was cooled down (ice bath), and arylsulfonyl chloride (0.46 mmol) was added at 0 C in one portion. The reaction mixture was stirred for 2-6 h under cooling. Then, the solvent was evaporated and the sulfonamides were purified using silica gel column with CH2Cl2/MeOH as an eluting system. Free bases were then converted into the hydrochloride salts by treatment of their solution in anhydrous ethanol with 1.25 M HCl in MeOH.; 9.2.6.8 1-Methyl-N-(1-{[2-(t-butyl-2-yl)phenoxy]ethyl}piperidin-4-yl)-N-methyl-1H-pyrazole-sulfonamide (17) Yellow oil, 80 mg following chromatographic purification over silica gel with CH2Cl2/MeOH (9:0.7); LC/MS purity 100%, tR = 4.81, C22H34N4O3S, MW 434.60, Monoisotopic Mass 434.24, [M+H]+ 435.5. 1H NMR (300 MHz, CDCl3) delta 1.37 (s, 9H), 1.50-1.58 (m, 2H), 1.70 (qd, J = 12.17, 3.89 Hz, 2H) 2.19 (td, J = 11.80, 2.23 Hz, 2H), 2.73 (s, 3H), 2.82 (t, J = 6.07 Hz, 2H), 2.97-3.04 (m, 2H), 3.76-3.88 (m, 1H), 3.93 (s, 3H), 4.06 (t, J = 6.06 Hz, 1H), 6.83 (dd, J = 8.21, 1.03 Hz, 1H), 6.87-6.91 (m, 1H), 7.15 (td, J = 7.71, 1.70 Hz, 1H), 7.27 (dd, J = 7.92, 1.44 Hz, 1H), 7.70 (s, 1H), 7.74 (s, 1H). 13C NMR (75 MHz, CDCl3) delta 28.58, 29.28, 29.68, 29.81, 34.81, 39.55, 53.48, 55.09, 57.13, 65.94, 112.03, 120.39, 122.24, 126.64, 126.97, 131.35, 138.10, 138.15, 157.49. Anal. calcd for C22H34N4O3S·2HCl: C: 52.06, H: 7.15, N: 11.04, S: 6.32; Found C: 51.95, H: 6.95, N: 10.82, S: 6.11. Mp for C22H34N4O3S·2HCl: 181.7-182.3 C.

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:
Article; Canale, Vittorio; Kurczab, Rafa?; Partyka, Anna; Sata?a, Grzegorz; S?oczy?ska, Karolina; Kos, Tomasz; Jastrz?bska-Wi?sek, Magdalena; Siwek, Agata; P?kala, Elzbieta; Bojarski, Andrzej J.; Weso?owska, Anna; Popik, Piotr; Zajdel, Pawe?; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 130 – 139;,
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. 400877-57-8, name is Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate

A mixture of [1-METHYL-4-NITRO-LH-PYRAZOLE-3-CARBOXYLIC] acid methyl ester (500 mg, 2.7 mmol) and 10% palladium on carbon [(50] mg) in methanol [(25] mL) was subjected to 60 psi pressure of hydrogen gas in a Parr apparatus for 24 h. At this time, the reaction mixture was filtered through a pad of celite and washed with methanol. The filtrate was concentrated in vacuo to afford [4-AMINO-1-METHYL-LH-PYRAZOLE-3-] carboxylic acid methyl ester (402 mg, 96%) as an off-white solid

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; F. HOFFMANN-LA ROCHE AG; WO2003/106459; (2003); 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. 25699-83-6, name is 4-(1H-Pyrazol-1-yl)benzonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 25699-83-6

A 250-mL round-bottom flask was charged with 4-(1H-pyrazol-1-yl)benzonitrile (Step 1, 2 g, 11.82 mmol), ethanol (40 mL), water (40 mL) and sodium hydroxide (705 mg, 17.63 mmol,). The resulting solution was stirred at 105 C. 16 h and then concentrated under vacuum. The residue was diluted with water (30 mL) and extracted with ethyl acetate (50 mL). The pH of the aqueous phase was adjusted to 5 with hydrochloric acid (6.0 M). The solids were collected by filtration, washed with water (10 mL) and dried in an oven to afford 4-(1H-pyrazol-1-yl)benzoic acid as a light yellow solid (Intermediate 2-13, 1 g, 45%). LCMS: (ESI) m/z 189 [M+H].

The synthetic route of 25699-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Forma Therapeutics, Inc.; Ioannidis, Stephanos; Talbot, Adam Charles; Follows, Bruce; Buckmelter, Alexandre Joseph; Wang, Minghua; Campbell, Ann-Marie; (61 pag.)US2016/185786; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics