Day: September 14, 2021

Some common heterocyclic compound, 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, molecular formula is C6H7IN2O2, 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. Recommanded Product: Ethyl 4-iodo-1H-pyrazole-5-carboxylate

At 0C, NaH (902.12 mg, 22.55 mmol, 60%) was added portionwise into a solution of Example 1A (5 g, 18.79 mmol) in DMF (30 mL) and stirred for 30 min. A solution of dibromodifluoromethane (9.00 g, 42.89 mmol) in DMF (30 mL) was added and stirred at 20C for 16 h. The reaction solution was quenched with water (100 mL) and extracted with ethyl acetate (50 mL * 3). The combined organic phase was washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and evaporated to give a residue. The residue was purified by column chromatography to give the title compound as a brown liquid (2 g, 26.95%). 1H NMR (400 MHz, CHLOROFORM-d) delta=8.00 (s, 1H), 4.48 (q, J=7.3 Hz, 2H), 1.45 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 179692-08-1, its application will become more common.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; LIU, Shilan; WANG, Dahai; LIANG, Guibai; HU, Guoping; LI, Jian; CHEN, Shuhui; (167 pag.)EP3418282; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 152120-54-2, A common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, molecular formula is C14H22N4O4, 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 N-alpha-Boc-D-lysine (13.0 g, 52.7 mmol) in EtOH (290 mL) was added N,N’-bis-Boc-1-guanylpyrazole (16.3 g, 52.7 mmol) and triethyl amine (10.6 g, 105 mmol). The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was purified by column chromatography (silica gel, 10:1 CH2Cl2/MeOH) to afford a pyrazole salt (25.0 g) as colorless oil. _The salt was dissolved in 1 N NaOH (300 mL) and neutralized with 1 N HCl (305 mL) The resulting precipitate was filtered out and dried, to afford compound 3 (22.0 g, 85%) as a white solid: 1H NMR (400 MHz, CDCl3) delta 11.48 (br s, 1H), 8.35 (br s, 1H), 5.23 (d, J=7.5 Hz, 1H), 4.23 (br s, 1H), 3.48-3.25 (m, 2H), 1.96-1.50 (m, 6H), 1.51 (s, 9H), 1.49 (s, 9H), 1.43 (s, 9H).

The synthetic route of 152120-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PARION SCIENCES, INC.; JOHNSON, Michael Ross; THELIN, William Robert; BOUCHER, Richard C.; US2013/324559; (2013); 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. 1151802-23-1, name is 4-Bromo-1-cyclopropyl-1H-pyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 1151802-23-1

General procedure: A suspension of 1 -Difluoromethyl-4-(4,4,5,5 -tetramethyl-[ 1,3,21 dioxaborolan-2-yl)- 1H-pyrazole (1.47 g, 6.03 mmol), 4-bromo-2,6-difluorobenzaldehyde (1.1 g, 4.98 mmol), palladium acetate (0.03 g, 0.12 mmol), butyldi-1-adamantylphosphine (0.11 g, 0.3 mmol), and potassium carbonate (2.06 g, 14.93 mmol) in water (7 ml) and 1,4-dioxane (22 ml) in a tube was degassedfor 10 mm with argon, then the tube was sealed and heated at 100 C overnight. The reaction mixture was cooled to room temperature, concentrated under reduce pressure, the residue was diluted with EtOAc and washed with brine 2x then dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (10% to 25% EtOAc/Hex) to afford P7. 1HNMR (400 MHz, Chloroform-d) oe 10.32 (s, 1H), 8.16 (s,1H), 7.96 (s, 1H), 7.23 (t, J = 60.4 Hz, 1H), 7.14 (d, J = 9.5 Hz, 2H).

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; GILEAD SCIENCES, INC.; BACON, Elizabeth M.; CHIN, Elbert; COTTELL, Jeromy J.; KATANA, Ashley Anne; KATO, Darryl; LINK, John O.; SHAPIRO, Nathan; TREJO MARTIN, Teresa Alejandra; YANG, Zheng-Yu; (395 pag.)WO2018/145021; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 500011-84-7, These common heterocyclic compound, 500011-84-7, name is 3-Bromo-1-(dimethylsulfamoyl)pyrazole, 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.

Step 3: Preparation of 3-bromo-lff-pyrazole; To 3-bromo-pyrazole-l-sulfonic acid dimethylamide (21.3 g) was slowly added trifluoroacetic acid (30 mL) and stirred at room temperature for 2 h. Hexane was added and the formed precipitate was filtered off and washed with hexane. The filtrate was diluted with MTB-ether, washed with sat. NaHC03-solution, water and brine, dried over MgSO4 and concentrated in vacuum to afford 10.7 g of a colorless oil containing 80% of the title compound of the formulaBrH The residue was used for the next step without further purification .1H-NMR (CDCl3, TMS) 8 (ppm) : 6.37 (IH, d, J = 3 Hz), 7.55 (IH, d, J = 3 Hz), 12.6 (IH, br s).

The synthetic route of 500011-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 25016-20-0, 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. 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Acid R2a (9.03 mg; 0.072 mmol) is dissolved in DMF (2 mL) and TEA (33.3 muIota 0.072 mmol) and TBTU (23.0 mg; 0.072 mmol) are added and the mixture is stirred for 15 mins. The Boc de-protected macrocyclic amine hydrochloride Ch is dissolved in DMF (1.0 mL) and added to the acid solution and stirred at RT overnight. The resulting solution is filtered through a Millex filter and purified by prep HPLC (ammonium bicarbonate/MeOH). The pure fractions are combined, concentrated, frozen and lyophilized to provide compound 1029.FIA M.S.(electrospray) : 858.3 (M-H)”, 860.2 (M+H)+ Retention time (min): 6.9 min1H NMR (400 MHz,DMSO-d6): delta 10.83 (s, 1H) , 8.93 (s, 1H), 7.90 (d, 1H, J= 9 Hz), 7.79 (d, 1H, J= 7Hz), 7.75 (d, 1H, J= 2.4 Hz), 7.16 (d, 1H, J= 9 Hz), ), 6.61 (s, 1H), 6.57 (d, 1H, J =2.3 Hz), 5.65-5.58 (m 1H), 5.52 (m, 1H), 5.20-5.04 (m, 3H), 4.61- 4.54 (m, 2H), 4.43-4.39 (m, 2H), 4.05-4.00 (m, 2H), 3.89 (d,6H, J = 5.8Hz), 2.67- 2.60 (m, 1H), 2.45 (s, 3H), 2.40-2.29 (m, 2H), 1.97-1.91 (m, 1H), 1.83-1.75 (m, 1H), 1.60-1.49 (m, 3H), 1.43-1.33 (m, 7H), 1.32-1.23 (m, 3H), 0.92-0.84 (m= 2H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Methyl-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET, Montse; BORDELEAU , Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63501; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, 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 285984-25-0, category: pyrazoles-derivatives

To a solution of CDI (510 mg, 3.15 mmol) in dry DCM (6.0 mL) at RT was added Intermediate A1 (722 mg, 3.15 mmol) portionwise over 15 min and the reaction mixture maintained at RT for 20 hr. An aliquot of the resulting solution (840 mu, 0.44 mmol) was added to a solution of Intermediate M1 , (81 mg, 0.21 mmol) in dry DCM (4.0 mL) and the reaction mixture was maintained at RT for 1 day and was then partitioned between saturated aq. NaHC03 (20 mL) and DCM (20 mL). The aq layer was separated and extracted with DCM (20 mL) and the combined organic extracts were dried and evaporated in vacuo. The residue was purified by flash column chromatography (Si02, 12 g, [1 % NH3 in MeOH] in DCM, 0-10%, gradient elution) to provide the title compound, Example 24, as a white solid (53 mg, 37 %); Rl 5.39 min (Method 1 basic); m/z 640/642 (M+H)+, (ES+); 1H NMR (400 MHz, DMSO-de) delta: 1.27 (9H, s), 2.16 (6H, s), 2.33 (2H, t), 2.34 (3H, s), 3.21 (2H, td), 6.38 (1 H, s), 7.23-7.28 (2H, overlapping m), 7.33-7.37 (3H, overlapping m), 7.41 (2H, m), 8.08 (1 H, d), 8.35 (1 H, d), 8.83 (1 H, br s), 9.17 (1 H, br s), 9.68 (1 H, br s).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RESPIVERT LIMITED; KING-UNDERWOOD, John; HARDY, George; MURRAY, Peter John; WILLIAMS, Jonathan Gareth; ONIONS, Stuart Thomas; WO2011/121366; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 285984-25-0,Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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 stirred solution of CDI (223 mg, 1 .38 mmol) in dry DCM (3.5 mL) was added Intermediate A1 (315 mg, 1 .38 mmol) as a solid, portion-wise, over 12 min and the resulting solution maintained at RT for 4 hr. An aliquot of this solution (2.0 mL, 0.79 mmol) was added to a solution of Intermediate G1 , (140 mg, 0.39 mmol) in dry THF (5.0 mL), and the reaction mixture was kept at RT for 17 hr and was then partitioned between saturated aq. NaHC03 (30 mL) and DCM (30 mL). The aq. layer was extracted with DCM (30 mL) and the combined organic extracts were dried and evaporated in vacuo. The residue was purified by flash column chromatography (Si02, 12 g, [5% MeOH in EtOAc] in isohexane, 0-45%, gradient elution) to afford the title compound, Example 14, as an off white solid (127 mg, 52%); R’ 5.40 min (Method 1 basic); m/z 61 1/613 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) delta: 1 .26 (9H, s), 2.37 (3H, s), 3.37 (3H, s), 4.07 (2H, s), 5.31 (2H, s), 6.34 (1 H, s), 7.18-7.23 (2H, overlapping m), 7.31 -7.34 (2H, overlapping m), 7.38-7.40 (2H, overlapping m), 7.85 (1 H, d), 8.21 (1 H, br s), 8.33 (1 H, dd), 8.60 (1 H, br s), 8.95 (1 H, br s), 10.01 (1 H, br s).

The synthetic route of 285984-25-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESPIVERT LIMITED; KING-UNDERWOOD, John; HARDY, George; MURRAY, Peter John; WILLIAMS, Jonathan Gareth; ONIONS, Stuart Thomas; WO2011/121366; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 660845-30-7, 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. 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 500 mL round-bottom flask, 6.0 g (31 mmol) of 5-chloro-3-(difluoromethyl)-1 -methyl-1 H- pyrazole-4-carbaldehyde were taken up in 30 mL of toluene. A solution of 2.4 g (62 mmol) of sodium hydroxide in 6 mL of water was added to the reaction mixture, followed by 103 mL of a 30% strength solution of hydrogen peroxide in water. During the addition, the temperature was kept below 37 C. The reaction mixture was then stirred at 50 C for 7 h. After cooling, the organic phase was extracted with 100 mL of water. The aqueous phase was acidified to pH 2 using dilute hydrochloric acid. The white precipitate formed was filtered off, washed twice with 20 mL of water and dried. This gave 3.2 g of 5-chloro-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carboxylic acid as a white solid. H NMR (400 MHz, DMSO-c/6) delta ppm : 3.78 (s, 3H); 7.12 (t, 1 H, JHF = 53.60 Hz); 13.19 (s, 1 H); IR (KBr): 1688 cm”1 (C=0); 2200-3200 cm”1 broad;

The synthetic route of 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; BENTING, Juergen; DESBORDES, Philippe; GARY, Stephanie; GREUL, Joerg; TSUCHIYA, Tomoki; WACHENDORFF-NEUMANN, Ulrike; WO2012/65944; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 26621-44-3, name is 3-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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 C3H3N3O2

Production Example 405 4-Bromo-3-nitro-1-trityl-1H-pyrazole 1.42 ML bromine was added at room temperature to a mixture of 3.13 g 3-nitro-1H-pyrazole (compound described in Janssen et al., J. Org. Chem., 36, 3081 (1971)) and 60 ML acetic acid, and the mixture was stirred for 6 hours.. Iced water was added to the reaction solution which was then neutralized with 5 N aqueous sodium hydroxide and an aqueous saturated ammonium chloride solution.. By adding ethyl acetate and water, the aqueous layer was separated.. The aqueous layer was saturated with common salt and extracted with ethyl acetate.. The combined organic layer was washed with an aqueous brine and then dried over anhydrous sodium sulfate.. The drying agent was filtered off, and the filtrate was evaporated. 5.41 g crude product of 4-bromo-3-nitro-1H-pyrazole was obtained as pale brown crystals.. From this compound, 11.05 g of the title compound was obtained as pale brown crystals by the same method as in Production Example 15.1H-NMR (CDCl3) delta: 7.10(m, 6H), 7.27-7.40(m, 9H), 7.46(s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 26621-44-3, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; EP1382603; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 92933-47-6, 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. 92933-47-6, name is 5-Isopropyl-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of HATU (174.17 mg, 0.459 mmol) and 3-isopropylpyrazole-5-carboxylic acid (59.85 mg, 0.388 mmol) in DMF (2 mL) was then added diisopropylethylamine (92 muL, 0.529 mmol). The reaction solution was stirred at room temperature for 2 h. The N-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)benzamide (100 mg, 0.353 mmol) was added in one portion. The solution was then stirred at room temperature overnight. The reaction was diluted with methylene chloride and washed. The aqueous layer was extracted with methylene chloride twice, the combined organic phases were dried over anhydrous MgSO4. After evaporation of the solvent and recrystallization from ethyl acetate, filtered and dried to give desired compound (50 mg, 34%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Isopropyl-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nam, Mina; Kim, TaeHun; Kwak, Jinsook; Seo, Seon Hee; Ko, Min Kyung; Lim, Eun Jeong; Min, Sun-Joon; Cho, Yong Seo; Keum, Gyochang; Baek, Du-Jong; Lee, Jiyoun; Pae, Ae Nim; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 245 – 258;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics