Tag: M.W:100-200

Electric Literature of 37622-90-5, A common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, 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.

4-Ethylpyrazole carboxylate (10g, 71.40 mmol) is placed in an oven -dried flask under an atmosphere of argon. Dry THF (100 mL) is added followed by the dropwise addition of lithium aluminium hydride (1 M in THF, 100 mL, 100 mmol). Once the addition is complete the reaction mixture is stirred at 50C. The reaction is shown to be complete by NMR after 4 hours. The reaction mixture is cooled on an ice-bath and the reaction mixture is quenched with water (3.8 mL) then 15% sodium hydroxide (3.8 mL) and finally water again (11.4 mL). The solvent is removed in vacuo and the solid is placed in a Soxhlet apparatus. THF is refluxed through the system for 24 hours. The solvent is removed in vacuo to give the title compound.1H NMR (MeOD, 400 MHz); 7.60 (s, 2H), 4.55 (s, 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; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2008/6563; (2008); 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. 52867-42-2, name is Methyl 2-methyl-5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2O3

Example 782-Methyl-5-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid isopropylamidea) 2-Methyl-5-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl esterTo a stirred solution of 5-hydroxy-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (355 mg, 2.28 mmol) and (5-methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanol (432 mg, 2.28 mmol) in THF (10 mL) at 5 0C under argon was added triphenylphosphine (775 mg, 2.95 mmol), then diethyl azodicarboxylate (515 mg, 2.95 mmol) was added dropwise. The reaction mixture was warmed to room temperature overnight. Then the reaction mixture was evaporated and purified by chromatography (silica, heptane:ethyl acetate = 1 :1 to 7.5:2.5) to afford the title compound (220 mg, 30%) as a white solid. MS: m/e = 329.3 [M+H]+.

The synthetic route of 52867-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JAKOB-ROETNE, Roland; LUCAS, Matthew, C.; THOMAS, Andrew; WO2010/127975; (2010); 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. 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H9N3O2

General procedure: A mixture of ethyl-5-amino-1H-pyrazole-4-carboxylate 1 (1.0 mmol), an appropriate aldehyde 2 (1.0 mmol) and aterminal alkyne 3 (1.0 mmol) in acetic acid (5 mL) was stirred at 25 °C for 10 min. The mixture was then stirred at 60 °C under ultrasound using a laboratory ultrasonic bath SONOREX SUPER RK 510H model producing irradiationof 35 kHz for 30 min in the presence of air. The increase of bath temperature beyond 60 °C due to the prolonged ultrasound irradiation was controlled by adding cold water time to time. After completion of the reaction the mixture was cooled to room temperature, poured into ethyl acetate (25 mL) and washed with brine solution (2 x 15 mL) followed by 10percent NaHCO3 solution (2 x 15 mL). The organiclayer was collected, dried over anhydrous Na2SO4, filteredand concentrated under low vacuum. The residue isolatedwas purified by column chromatography over silica gel using3-8percent petroleum ether-EtOAc to give the desired product.

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 1260243-04-6.

Reference:
Article; Suresha, Namburi; Durgaraoa, Bodapati Veera; Ratnakar; Kolli, Sunder Kumar; Ashfaq, Mohd Ashraf; Rao, Mandava V. Basaveswara; Pal, Manojit; Letters in drug design and discovery; vol. 14; 10; (2017); p. 1176 – 1183;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 31728-75-3,Some common heterocyclic compound, 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-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.

mixture of 4-(6-(4-amino-4-methylpiperidin-l-yl)pyridin-3-yl)-6-(2-hydroxy-2- methylpropoxy)pyrazolo[l,5-a]pyridine-3-carbonitrile dihydrochloride (Intermediate P46; 50 mg, 0.12 mmol), HATU (54 mg, 0.14 mmol), l,5-dimethyl-lH-pyrazole-4-carboxylic acid (25 mg, 0.18 mmol) in DCM (2.4 mL) was treated with DIEA (104 mu,, 0.59 mmol) and then stirred for 16 h at ambient temperature. The reaction mixture was diluted with DCM and washed with saturated NaHCCb. The organic extracts were dried over anhydrous Na2S04(s), filtered and concentrated in vacuo. The reaction was purified by silica chromatography (1-10% MeOH in EtOAc as the gradient eluent) to cleanly provide the title compound (41.9 mg, 63.2% yield) MS (apci) m/z= 543.20 (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 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, its application will become more common.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COLLIER, James; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; RAMANN, Ginelle A.; TANG, Tony P.; REN, Li; WALLS, Shane M.; (946 pag.)WO2018/71454; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 82560-12-1, These common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, 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.

3-(tert-butyl)-lH-pyrazole-5-amine (503 mg, 3.61 mmol), Intermediate 30b (915 mg, 3.44 mmol), copper (I) iodide (32.8 mg, 0.172 mmol), trans- N,N’-dimethylcyclohexane- l ,2-diamine (97.8 mg, 0.688 mmol) and K2CO3 (998 mg, 7.22 mmol) were weighed in a round bottom flask, sealed with a septum and evacuated and purged with Ar 3 times. Xylene (4 ml, sparged with Ar for 45 min), was then introduced to the flask and the brown suspension was heated to 150C for 90 min. The reaction was cooled, diluted with EtOAc (10 mL), water (10 mL) and saturated aqueous NH4OH solution (5 mL). The aqueous layer was extracted with EtOAc (2 x 10 mL), and the combined organics washed with brine (15 mL), dried over Na2SO4, filtered, concentrated in vacuo and subjected to FCC eluting with 0 – 4% MeOH/EtOAc to afford the title compound as a pale yellow solid (457 mg, 48%). LCMS (Method 4): Rt 2.81 min, m/z 278 [MH+].

Statistics shows that 3-Amino-5-tert-butylpyrazole is playing an increasingly important role. we look forward to future research findings about 82560-12-1.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; PANCHAL, Terry Aaron; JENNINGS, Andrew Stephen Robert; CRIDLAND, Andrew Peter; HURLEY, Christopher; WO2014/194956; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 35100-92-6,Some common heterocyclic compound, 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine, molecular formula is C5H9N3, 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: To a solution of benzoic acid which was obtained by hydrolysis of methyl esters 8 or 12A-E (0.22 mmol, 1.0 equiv), aminothiazole or imidazo[1,2-a]pyrazin-8-amine or aminopyrazole (0.33 mmol, 1.5 equiv), HATU (0.33 mmol, 1.5 equiv) and HOAt (0.33 mmol, 1.5 equiv) in DMF (2 mL) was added dropwise di(isopropyl)ethylamine (DIPEA) (0.12 mL, 0.67 mmol, 3 equiv). The reaction was run under microwave at 60 C (40 W) for 30 min, and then cooled to room temperature and poured into brine. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous NaSO4 and concentrated. The residue was purified by chromatography (SiO2, petroleum ether/EtOAc = 4:1-1:1) to yield corresponding amides as white or yellow powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,5-Dimethyl-1H-pyrazol-3-amine, its application will become more common.

Reference:
Article; Mao, Weiwei; Ning, Mengmeng; Liu, Zhiqing; Zhu, Qingzhang; Leng, Ying; Zhang, Ao; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 2982 – 2991;,
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. 478968-48-8, name is Ethyl 3-methoxy-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C7H10N2O3

(6-{3-Azabicyclo[3. 1 .0]hexan-3-yl}-2-methylpyridin-3-yl)methanol (410 mg), tributylphosphine (595 pL) and ethyl 3- methoxy-1H-pyrazole-4-carboxylate (340 mg) are dissolved in tetrahydrofuran (10 mL), cooled to -10 00 and treated with di-tert.-butyl azodicarboxylate (DBAD, 510 mg). Then the mixture is stirred for 30 minutes at room temperature. The mixture is purified by HPLC on reversed phase (acetonitrile, water, ammonia) to give the title compound.LC (Method 8): tR = 1.09 mm; Mass spectrum (ESIj: mlz = 357 [M+H].

The synthetic route of 478968-48-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FRATTINI, Sara; LINGARD, Iain; HAMPRECHT, Dieter, Wolfgang; BAKKER, Remko, Alexander; ECKHARDT, Matthias; GOLLNER, Andreas; HEHN, Joerg, P.; LANGKOPF, Elke; WAGNER, Holger; WELLENZOHN, Bernd; WIEDENMAYER, Dieter; (90 pag.)WO2018/192866; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 52222-73-8, 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. 52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a room temperature solution of C5 (100 mg, 0.208 mmol) in N,N-dimethylformamide (2 mL) was added cesium carbonate (170 mg, 0.522 mmol), followed by 4-(trifluoromethyl)-1H-pyrazole (42.5 mg, 0.312 mmol), and the reaction mixture was stirred at 80 C. overnight. It was then partitioned between water and ethyl acetate, and the aqueous layer was extracted with ethyl acetate (3*15 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 0% to 25% ethyl acetate in heptane) provided the product as an oil. Yield: 71 mg, 0.13 mmol, 62%. LCMS m/z 536.4 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.74 (s, 1H), 7.69 (s, 1H), 7.25 (br d, J=8.6 Hz, 2H), 6.88 (br d, J=8.6 Hz, 2H), 5.54-5.44 (m, 1H), 4.78 (quint, J=8.4 Hz, 1H), 4.51 (AB quartet, JAB=11.7 Hz, DeltanuAB=28.5 Hz, 2H), 3.81 (s, 3H), 3.76 (dd, half of ABX pattern, J=11.3, 3.9 Hz, 1H), 3.69 (br dd, half of ABX pattern, J=10.9, 7.0 Hz, 1H), 3.55-3.47 (br m, 2H), 3.47-3.38 (br m, 2H), 2.52-2.42 (m, 2H), 2.38 (dd, half of ABX pattern, J=12.5, 8.6 Hz, 2H), 1.76-1.62 (br m, 4H).

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

Reference:
Patent; PFIZER INC.; BRODNEY, MICHAEL AARON; BUTLER, CHRISTOPHER RYAN; MCALLISTER, LAURA ANN; HELAL, CHRISTOPHER JOHN; O’NEIL, STEVEN VICTOR; VERHOEST, PATRICK ROBERT; (103 pag.)US2018/208607; (2018); 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. 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 139756-02-8

To a 250 ml three-mouth bottle by adding 2 – ethoxy formaldehyde 7.63 g, 1 – methyl -3 – propyl -4 – amino pyrazole -5 – carboxamide 9.6 g and isopropyl alcohol 150 ml, stir at room temperature 3 hours; adding 8.56 g anhydrous ferric trichloride, stirring which separate the reaction system access oxygen, temperature 60 C reaction 3 hours; boil off isopropanol about 100 ml, adding 180 ml purified water, filtered, drying to obtain the solid 14.8 g. Yield: 92.8%.

The synthetic route of 139756-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Tongjuan Pharmaceutical Technology Co., Ltd.; Zheng Qingquan; Huang Shifu; Cao Xutao; Li Yongjian; (10 pag.)CN104804003; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 89501-90-6, name is 1-Methyl-1H-pyrazole-3-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. Quality Control of 1-Methyl-1H-pyrazole-3-sulfonyl chloride

Ui) l-Methyl-lH-pyrazole-3-sulfonic acid benzyl-(l-oxo-l,2,3,4-tetrahydro- isoquinolin-6-yl)-amideTo a stirred solution of 6-benzylamino-3,4-dihydro-2H-isoquinolin-l-one (45 mg, 0.18 mmol) and pyridine (31 mul, 0.39 mmol) in anhydrous acetonitrile (1 ml) was added 1- methyl-lH-pyrazole-3-sulfonyl chloride (70 mg, 0.39 mmol) and the reaction heated to 1500C in a microwave for 0.5 hrs. The solvent was evaporated in vacuo and the crude residue purified by preparative tic (5% methanol in dichloromethane) to afford the title compound as a yellow solid (10 mg, 14%). HPLC retention time 3.83 min. Mass spectrum (ES+) m/z 397 (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 89501-90-6, its application will become more common.

Reference:
Patent; XENTION LIMITED; HAMLYN, Richard, John; MADGE, David; MULLA, Mushtaq; WO2010/139953; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics