Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 37718-11-9, name is 1H-Pyrazole-4-carboxylic acid, 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 37718-11-9, Computed Properties of C4H4N2O2

To the stirred solution of lH-pyrazole-4-carboxylic add 19-1 (20 g, 178.43 mmol) in methanol (100 niL) was added H2SO4 (17.50 g, 178.43 mmol, 9.51 rnL) at 0C and the reaction mixture was refluxed for 16 hours at 80C. Solvent was evaporated and the crude material was neutralized by saturated sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate and washed with brine. After separation, the organic layer was dried over sodium sulfate and evaporated to obtain methyl lH-pyrazole-4-earboxylate 19-2 (21 g, 166.52 mmol, 93.32% yield) as white solid. LC MS: ES+127.0.

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Reference:
Patent; C4 THERAPEUTICS, INC.; VEITS, Gesine, Kerstin; HE, Minsheng; HENDERSON, James, A.; NASVESCHUK, Christopher, G.; PHILLIPS, Andrew, J.; GOOD, Andrew, Charles; (471 pag.)WO2019/191112; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 400755-44-4,Some common heterocyclic compound, 400755-44-4, name is 1-Ethylpyrazole-3-carboxylic Acid, molecular formula is C6H8N2O2, 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 242 Production of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1-ethyl-1H-pyrazole-3-carboxamide Using 1-ethyl-1H-pyrazole-3-carboxylic acid (128 mg, 0.92 mmol), tetrahydrofuran (2.0 mL), N,N-dimethylformamide (20 muL, 0.26 mmol), oxalyl chloride (80 muL, 0.92 mmol), N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (200 mg, 0.61 mmol) and N,N-dimethylacetamide (4.0 mL), and in the same manner as in Example 238, the title compound (111 mg, 40%) was obtained as a white powder. 1H-NMR (DMSO-d6, 300 MHz) delta 0.76-0.85 (4H, m), 1.44 (3H, t, J=7.2 Hz), 1.87-1.97 (1H, m), 4.26 (2H, q, J=7.2 Hz), 6.77 (1H, d, J=2.1 Hz), 7.07 (1H, d, J=9.6 Hz), 7.09-7.16 (1H, m), 7.39 (1H, dd, J=11.4, 8.7 Hz), 7.84 (1H, dd, J=6.5, 2.9 Hz), 7.91-7.96 (2H, m), 8.04 (1H, d, J=9.6 Hz), 9.57 (1H, s), 11.07 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Ethylpyrazole-3-carboxylic Acid, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 42027-81-6, name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, molecular formula is C5H7N3O3, 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 C5H7N3O3

General procedure: To 17a (1 g, 7.8 mmol) in EtOH (20 mL) was added 10% Pd/C50 mg. The reaction mixture was stirred for 3 h under hydrogen at roomtemperature. The mixture was then filtered with Celite, and the filtratewas concentrated and dried under vacuum to yield 0.74 g (97%) of 18aas a white solid. MS (ESI) m/z 98 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42027-81-6, its application will become more common.

Reference:
Article; Yu, Ru-Nan; Chen, Cheng-Juan; Shu, Lei; Yin, Yuan; Wang, Zhi-Jian; Zhang, Tian-Tai; Zhang, Da-Yong; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1646 – 1657;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35691-93-1, name is Ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate, 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 35691-93-1, HPLC of Formula: C8H12N2O2

3,5-Dimethyl-1H-pyrazole-carboxylic acid ethyl ester(0.83 g, 5 mM), potassium carbonate (2.07 g, 15 mM), tetrabutylammonium bromide(0.11 g, 0.25 mM), and ethyl bromoacetate (3.32 mL, 5 mM) were mixed in 1,4-dioxane(60 mL). The reaction mixture was stirred at 140 C for 24 h and the solvent was removedby evaporation. The residue was dissolved in CH2Cl2 (40 mL) and washed with deionized water (200 mL). The organic layer was dried over MgSO4 and evaporated to give 1-ethoxycarbonylmethyl-3,5dimethyl-1H-pyrazole-4-carboxylic acid ethyl ester (Ecmdpcaee) as afaint yellow oil. Yield: 0.78 g (78.7%). 1H NMR (CDCl3, 500 MHz) delta: 4.80 (s, 2H), 4.16(q, 2H), 4.24 (q, 2H), 2.47 (s, 3H), 2.42 (s, 3H), 1.36 (t, 3H), 1.28 (t, 3H); ESI-MS: m/z(%) 254.95 [MH+] (100%), 274.10[MK+] (100%); IR (cm-1, KBr pellet): 3378 (m), 2985 (vs), 2931 (vs), 2587 (w), 1735 (vs), 1702 (s), 1656 (w), 1552 (s), 1447 (m), 1374 (s), 1356 (w), 1282 (s), 1233 (vs), 1160 (w), 1051 (w), 873 (m), 686 (m); m.p.: 50-52 C.

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, Ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xia, Qinghong; Ren, Yanqiu; Cheng, Mei-Ling; Liu, Xiuxiu; Chen, Sheng; Zhai, Changwei; Liu, Qi; Journal of Coordination Chemistry; vol. 68; 10; (2015); p. 1688 – 1704;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol, molecular formula is C5H8N2O, 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. Quality Control of 1,3-Dimethyl-1H-pyrazol-5-ol

General procedure: Intermediate 7 (4mmol), dissolved in dry dichloromethane (60mL), and PCl5 (4.2mmol) were added and stirred at room temperature for 1h. The solvent was moved out under reduced pressure to afford acid chloride, the acid chloride was then dissolved in dry CH2Cl2 (60mL), Then 1-methyl-1H-pyrazol-5-ol (4mmol) and Et3N (4.8mmol) were added to the above solution, and stirred for a further 18-24hat room temperature. After adding dichloromethane (30mL), the resultant mixture was washed sequentially with 2N hydrochloric acid (100mL), saturated NaHCO3 and saturated NaCl and dried over Na2SO4. The rest of the solution was evaporated in vacuum and purified by silica gel column chromatography using gradient elution of ethyl acetate/hexane (V:V = 1:2) to obtain the desired intermediate 8 as a write powder (30%-70%). 4.1.10 1-methyl-1H-pyrazol-5-yl3-methyl-2-oxo-1-propyl-2,3-dihydro-1H-benzo[d] imidazole- 5-carboxylate Yield: 45%. m.p. 107-108C. 1H NMR (600MHz, CDCl3) delta 8.01 (dd, J=8.4, 1.2Hz, 1H), 7.77 (d, J=1.2Hz, 1H), 7.48 (d, J=1.8Hz, 1H), 7.10 (d, J=8.4Hz, 1H), 6.20 (d, J=1.8Hz, 1H), 3.92 (t, J=7.2Hz, 2H), 3.80 (s, 3H), 3.51 (s, 3H), 1.91-1.71 (m, 2H), 1.00 (t, J=7.8Hz, 3H). EI-MS (m/z): 314.18 (M)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5203-77-0, its application will become more common.

Reference:
Article; Xu, Yu-Ling; Lin, Hong-Yan; Ruan, Xu; Yang, Sheng-Gang; Hao, Ge-Fei; Yang, Wen-Chao; Yang, Guang-Fu; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 427 – 438;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 118430-73-2, 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 118430-73-2 as follows.

Step E: 1-(2-Aminobenzyl)-3-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-urea (5s): 5-tert-Butyl-2-methyl-2H-pyrazol-3-ylamine (10s) (4.8 g, 31 mmol) and carbonyl diimidazole (4.6 g, 32 mmol) were partially dissolved in DCE (100 mL) and heated at 70 C. for 2 hours. The reaction was cooled and 2-aminomethyl-phenylamine (9s) (4.2 g, 34 mmol) was added and the reaction was stirred 14 hours. The reaction was concentrated to remove the solvent and then partitioned between EtOAc and 0.5N HCl (60 mL). The organic phase was washed with NH4Cl and water and dried (MgSO4). The solution was concentrated and recrystallized from EtOAc (200 mL) to provide the desired product (5s) (4.6 g, 49% yield). 1H NMR (400 MHz, DMSO-d6) delta 8.31 (s, 1H), 6.98 (d, J=1.6 Hz, 1H), 6.96 (dt, J=7.8, 1.6 Hz, 1H), 6.63 (t, J=6.3 Hz, 1H), 6.59 (d, J=7.0 Hz, 1H), 6.48 (t, J=6.3 Hz, 1H), 5.93 (s, 1H), 5.07 (s, 2H), 4.12 (d, J=6.3 Hz, 2H), 3.51 (s, 3H), 1.16 (s, 9H).

According to the analysis of related databases, 118430-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Munson, Mark; Mareska, David A.; Kim, Youngboo; Groneberg, Robert D.; Rizzi, James; Rodriguez, Martha; Kim, Ganghyeok; Vigers, Guy; Rao, Chang; Balachari, Devan; Harvey, Darren; US2004/192653; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole, 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 143426-52-2, Recommanded Product: 143426-52-2

5 mmol of the compound IIIh was dissolved in 30 mL of DMF, followed by the addition of 11 mmol of cesium carbonate, to which was addedintermediate 5mmol at room temperature, and the reaction was refluxed for 13 hours.The resulting residue was purified by columnchromatography to obtain the title compound Ih

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-(4-(Chloromethyl)phenyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nantong University; Dai Hong; Shi Yujun; Yao Wei; Song Chan; Qian Hongwei; Wang Xianglong; Zhang Zhou; Han Xudong; (16 pag.)CN106946782; (2017); 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. 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

General procedure: Intermediate 7 (4mmol), dissolved in dry dichloromethane (60mL), and PCl5 (4.2mmol) were added and stirred at room temperature for 1h. The solvent was moved out under reduced pressure to afford acid chloride, the acid chloride was then dissolved in dry CH2Cl2 (60mL), Then 1-methyl-1H-pyrazol-5-ol (4mmol) and Et3N (4.8mmol) were added to the above solution, and stirred for a further 18-24hat room temperature. After adding dichloromethane (30mL), the resultant mixture was washed sequentially with 2N hydrochloric acid (100mL), saturated NaHCO3 and saturated NaCl and dried over Na2SO4. The rest of the solution was evaporated in vacuum and purified by silica gel column chromatography using gradient elution of ethyl acetate/hexane (V:V = 1:2) to obtain the desired intermediate 8 as a write powder (30%-70%). 4.1.10 1-methyl-1H-pyrazol-5-yl3-methyl-2-oxo-1-propyl-2,3-dihydro-1H-benzo[d] imidazole- 5-carboxylate Yield: 45%. m.p. 107-108C. 1H NMR (600MHz, CDCl3) delta 8.01 (dd, J=8.4, 1.2Hz, 1H), 7.77 (d, J=1.2Hz, 1H), 7.48 (d, J=1.8Hz, 1H), 7.10 (d, J=8.4Hz, 1H), 6.20 (d, J=1.8Hz, 1H), 3.92 (t, J=7.2Hz, 2H), 3.80 (s, 3H), 3.51 (s, 3H), 1.91-1.71 (m, 2H), 1.00 (t, J=7.8Hz, 3H). EI-MS (m/z): 314.18 (M)+.

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; Xu, Yu-Ling; Lin, Hong-Yan; Ruan, Xu; Yang, Sheng-Gang; Hao, Ge-Fei; Yang, Wen-Chao; Yang, Guang-Fu; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 427 – 438;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 4-Bromo-3,5-dimethylpyrazole

17.63 g (0.101 mol) of the above intermediate was dissolved in 300 mL of carbon tetrachloride,19.58 g (0.11 mol) of NBS and 0.1 g of benzoyl peroxide were added and heated under reflux for 0.5 h.Stop the reaction, filter after cooling. The filtrate was concentrated and the resulting residue was poured into water and extracted with dichloromethane.The extracted organic phase was washed with saturated brine, dried over anhydrous sodium sulfate,The resulting residue was purified by silica gel column chromatography (silica gel 100-200 mesh, eluent petroleum ether: ethyl acetate = 20: 1)To give 21.2 g of product as a yellow liquid in 84.3percent yield.

The synthetic route of 3398-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Agricultural Sciences Plant Protection Institute; Mei Xiangdong; Dong Mengya; Ning Jun; Zhe Dongmei; Zhang Tao; Zhang Lanxiang; Si Weijie; (13 pag.)CN104610249; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

27258-32-8, name is 1-Methyl-1H-pyrazole-3-carbaldehyde, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C5H6N2O

[00346] 55A. 3-((2-(4-bromophenyl)hydrazono)methyl)-l-methyl-lH-pyrazole: To a solution of (4-bromophenyl)hydrazine hydrochloride (1 150 mg, 5.04 mmol) and 1- methyl-lH-pyrazole-3-carbaldehyde (580 mg, 5.00 mmol) in DMF (5.1 mL) was added triethylamine (0.84 mL, 6.00 mmol). The mixture was stirred at rt under argon for 21 h, water (9 mL) was added and stirring was continued for 1 h. The solid that resulted was filtered, rinsed with water (5 mL) and dissolved in CH2C12 (120 mL). The CH2C12 solution was dried (Na2S04) and concentrated to provide 55A (1400 mg, 5.02 mmol, 100 percent yield) as a yellowish solid: lH NMR (400MHz, CDC13) d 7.76 (s, 1H), 7.63 (s, 1H), 7.34 (m, 3H), 6.97 (d, J= 8.8 Hz, 2H), 3.91 (s, 3H).

The synthetic route of 27258-32-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HERNANDEZ, Andres S.; ELLSWORTH, Bruce A.; EWING, William R.; CHEN, Bin; WO2014/78608; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics