Tag: M.W:100-200

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,
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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 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

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

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

Reference of 176969-34-9,Some common heterocyclic compound, 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H6F2N2O2, 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 7: Production of N-[2-[3-chloro-5-(cyclopropylethynyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide To a 1 ml solution of 68 mg of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid in dichloromethane, 10 mg of N,N-dimethylformamide and 66 mg of oxalyl chloride were added. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was dissolved in 1 ml of dichloromethane and, with stirring under cooling with ice, added dropwisely to a mixed solution of 100 mg of 2-amino-1-[3-chloro-5-(cyclopropylethynyl)pyridin-2-yl]ethanone-O-isopropyl oxime and 200 mg of potassium carbonate in 2 ml of dichloromethane and 2 ml of water. After completion of the dropwise addition, stirring was further continued for 1 hour at room temperature. After completion of the reaction, 10 ml of water was added to the reaction mixture, followed by extraction with dichloromethane (10 ml*1). The obtained organic layer was washed with water (10 ml*1), and then dehydrated and dried by using saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography by eluting it with ethyl acetate-hexane (2:3), to obtain 150 mg of the desired product as a pale yellow resinous substance (E/Z=2/1). 1H NMR (CDCl3, Me4Si, 300 MHz) b 8.45 and 8.43 (d, J=1.8 Hz, 1H), 7.88 and 7.82 (s, 1H), 7.68 and 7.66 (d, J=1.8 Hz, 1H), 7.12 (bs, 1H), 6.85 and 6.75 (t, J=54.2 Hz, 1H), 4.70 and 4.46 (d, J=6.1, 4.9 Hz, 2H), 4.47 and 4.36 (sep, J=6.3 Hz, 1H), 3.90 and 3.87 (s, 3H), 1.4-1.55 (m, 1H), 1.32 and 1.18 (d, J=6.3 Hz, 6H), 0.8-1.0 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, its application will become more common.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; KUWAHARA, Hidehito; HASUNUMA, Nakako; FUKAMI, Yasuhiro; (68 pag.)US2017/188580; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1621-91-6, name is 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. Recommanded Product: 1621-91-6

Dimethyl sulfate (236 g, 177 mL, 1.87 mol) was added dropwise over 45 min to a stirred solution of pyrazole-3-carboxylic acid (200 g, 1.78 mol) in 20% aqueous sodium hydroxide (850 mL) at 40 C. The reaction mixture was heated at 80 C for 2 h, cooled to room temperature, filtered, the filtrate acidified to pH 1 with concentrated HCI, the precipitate filtered, washed with water, and dried under vacuum to yield 1-methylpyrazole-5-carboxylic acid (85 g, 38%). The filtrate was concentrated in vacuo to 800 ML, extracted with chloroform (15X400 mL), the organic phase dried over anhydrous magnesium sulfate, concentrated in vacuo, and the residue recrystallized from isopropanol to yield 1-METHYLPYRAZOLE-3-CARBOXYLIC acid (74 g) as a white crystalline solid.

The synthetic route of 1H-Pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/58702; (2004); A2;,
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. 852227-86-2, name is 5-(Chloromethyl)-1,3-dimethyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Formula: C6H9ClN2

A solution of 7d (58 mg, 0.20 mmol, 1.0 equiv) in anhydrous DMF (0.8 mL) was treated with 60% sodium hydride (18 mg, 0.44 mmol, 2.2 equiv). After stirring at room temperature for 5 min, 5-(chloromethyl)-l,3-dimethyl-lH-pyrazole (63 mg, 0.42 mmol, 2.1 equiv) was introduced. Then the mixture was stirred at room temperature for 2 hours. The reaction was quenched with saturated aqueous NaHCO3. The resulting solution was extracted with ethyl acetate. The combined extracts were washed once with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-TLC (ethyl acetate/dichloromethane/ methanol 10/10/1, 2 runs) to afford compound 30 (50 mg, 50%) as a white solid. MS 505 (MH)+, 503 (M-H)”. Purity 99% (HPLC).

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; SEQUOIA PHARMACEUTICALS, INC.; WO2009/105776; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25711-30-2, name is 1,5-Dimethyl-1H-pyrazole-4-carbaldehyde, 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 25711-30-2, Quality Control of 1,5-Dimethyl-1H-pyrazole-4-carbaldehyde

Example 17 N4-[(trans-4-{[(1,5-dimethyl-1H-pyrazol-4-yl)methyl]amino}cyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine A mixture of N4-[(trans-4-aminocyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]-pyrimidine-2,4-diamine (100 mg, 0.23 mmol) and 1,5-dimethyl-1H-pyrazole-4-carbaldehyde (23 mg, 0.19 mmol) in CH2Cl2 (15 mL) was stirred at room temperature for 1 h. NaBH(OAc)3 (200 mg, 0.95 mmol) was then added to the reaction mixture and stirred for another 16 h. The reaction mixture was diluted with 1M Na2CO3 to pH 9-10 and the organic phase was separated. The aqueous phase was extracted with CH2Cl2. The combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 54 mg (52%) of the title compound as a pale yellow foam, m/z 549.7 [M+1]+

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, 1,5-Dimethyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US2006/25433; (2006); 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. 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide

Preparation of 4-[2-Propoxy Benzamido]-1-Methyl-3-Propyl-5-Carbamoyl Pyrazole To a solution of 25 g of 2-propoxy benzoic acid dissolved in dichloromethane, 66 g of thionyl chloride was added and stirred for 3 hours under reflux. After reaction was completed, the solvent and excessive thionyl chloride were distilled off under reduced pressure. To the residue was added 200 ml of dichloromethane (reaction solution 1). In another container, to 24 g of 1-methyl-3-propyl-4-amino-5-carbamoyl pyrazole in dichloromethane was added 13.4 g of triethylamine and 100 mg of dimethylaminopyridine and then cooled to 0 C., to which said reaction solution 1 was slowly added while maintaining the temperature of the solution at 0 C., and then stirred for 1 hour. The reaction mixture was successively washed with water, saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure to obtain a crude product and then triturated with hexane to give 39 g of the title compound. 1H NMR (CDCl3): 0.91(t,3H), 1.05(t,3H), 1.62(m,2H), 1.89(m,2H), 2.52(t,2H), 4.06(s,3H), 4.18(t,2H), 5.57(br s,1H), 7.09(m,2H), 7.52(m,1H), 7.73(br s,1H), 8.26(dd,1H), 9.45(br s,1H)

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 139756-02-8.

Reference:
Patent; Yoo, Moo-Hi; Kim, Won-Bae; Chang, Min-Sun; Kim, Soon-Hoe; Kim, Dong-Sung; Bae, Chul-Jun; Kim, Yong-Duck; Kim, Eun-Ha; US2003/176696; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics