Tag: M.W:100-200

Synthetic Route of 873191-23-2,Some common heterocyclic compound, 873191-23-2, name is 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole, molecular formula is C6H9BrN2, 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: The lycorine derivatives 10, 11 and 12 (0.1mmol) were dissolved in dry THF (10mL), and NaH (50mg, 2mmol) and 3-(bromomethyl)pyridine, 3-(Chloromethyl)-1,5-dimethyl-1H-pyrazole or 5-Bromomethyl-1,3-dimethyl-1H-pyrazole (1mmol) were added. The mixture was stirred at r. t. for 24h and quenched with H2O (50mL) in an ice bath. The solution was evaporated to remove the THF and extracted with CH2Cl2 (2×30mL). The organic layer was washed with saturated NaHCO3 and brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using petroleum ether-EtOAc as the eluent to afford compounds 5, 6, 7, 8 and 9.

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

Reference:
Article; Chen, Duozhi; Zhang, Heng; Jing, Chenxu; He, Xiaoli; Yang, Bijuan; Cai, Jieyun; Zhou, Yunfu; Song, Xiaoming; Li, Lin; Hao, Xiaojiang; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 1491 – 1499;,
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. 611239-23-7, name is tert-Butyl 1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl 1H-pyrazole-4-carboxylate

To a solution of N-benzhydryl-6-chloro-4-methoxynicotinamide (200 mg, 0.6 mmol) in dioxane (16 mL) were added tert-butyl 1H-pyrazole-4- carboxylate (100 mg, 0.6 mmol), CuT (56 mg, 0.3 mmol), Cs2CO3 (550 mg, 1.7 mmol) and N,N-dimethylglycine (64 mg, 0.6 mmol). The mixture was stirred at 120C overnight. When TLC showed the reaction completed, the mixture was filtered. The filtrate was diluted with water (20 mL) and extractedwith EtOAc (40 mL). The organic layer was washed with brine (20 mL), dried over sodium sulfate and concentrated under vacuum. The residue was purified by prep. TLC (EtOAc /PE=3:1) to afford tert-butyl 1 -(5 -(benzhydrylcarbamoyl)-4- hydroxypyridin-2-yl)- 1 H-pyrazole-4- carboxylate. ?H NIVIR (CDC13,400 IVIHz) 12.87 (s, 1H), 8.88 (s, 1H), 8.50 (s, 1H), 8.02 (s, 1H), 7.55-7.50 (m, 1H), 7.42-7.27 (m, 11H), 6.41 (d, J= 7.3 Hz, 1H), 1.57 (s, 9H). LC/IVIS (m/z):471 (M+H).

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; MERCK SHARP & DOHME CORP.; UJJAINWALLA, Fez; TAN, John Qiang; DANG, Qun; SINZ, Christopher J.; WANG, Ming; CHEN, Yili; CAI, Jiaqiang; DU, Xiaoxing; (41 pag.)WO2016/54806; (2016); 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. 40704-11-8, name is 3-Methyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

Methyl5-methyl-1H-pyrazole-4-carboxylate. To a solution of 3-methyl-1H-pyrazole-4-carboxylic acid (1.26 g, 10 mmol) in MeOH (100 mL) was added thionyl chloride (5.73 g, 48 mmol) at 0 C. The mixture was stirred for 12 h and then concentrated in vacuo. The residue was quenched with sat. aq. sodium bicarbonate solution and extracted with EtOAc (3X). The combined organic phase was dried over sodium sulfate, filtered and concentrated to provide methyl 3-methyl-1H-pyrazole-4-carboxylate (0.8 g, 57%).

The synthetic route of 40704-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gehling, Victor S.; Vaswani, Rishi G.; Nasveschuk, Christopher G.; Duplessis, Martin; Iyer, Priyadarshini; Balasubramanian, Srividya; Zhao, Feng; Good, Andrew C.; Campbell, Robert; Lee, Christina; Dakin, Les A.; Cook, Andrew S.; Gagnon, Alexandre; Harmange, Jean-Christophe; Audia, James E.; Cummings, Richard T.; Normant, Emmanuel; Trojer, Patrick; Albrecht, Brian K.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 17; (2015); p. 3644 – 3649;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 96450-53-2,Some common heterocyclic compound, 96450-53-2, name is 1-(2-Chloroethyl)-1H-pyrazole, molecular formula is C5H7ClN2, 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 methyl 2,6-dioxo-l,2,3,6-tetrahydropyrimidine-4-carboxylate (900 mg, 5.29 mmol) was added DMF (17 mL). The mixture was cooled with an ice bath and lithium hydride (66.4 mg, 7.94 mmol) was then added in portions. The mixture was stirred for 20 minutes and ((chloromethoxy)methyl)benzene (0.899 mL, 5.82 mmol) in DMF (3 mL) was then added slowly via syringe. The mixture was stirred a 00C for 30 minutes. Lithium hydride (66.4 mg, 7.94 mmol) was then added in portions and stirred for 10 minutes. Sodium iodide (793 mg, 5.29 mmol) and l-(2-chloroethyl)-l/f-pyrazole (829 mg, 6.35 mmol) were added in portions and then stirred at 00C for 30 minutes. The ice bath was removed. The mixture was stirred at room temperature for 4 hours and then heated to 500C with stirring for 3 days. The reaction mixture was cooled to room temperature. Water (25 mL) and methanol (25 mL) were added and the solvents were evaporated under vacuum at 65C to give a residue, which was partitioned between IN NaOH (75 mL) and diethyl ether (50 mL). The organic layer was separated and the aqueous layer was washed with diethyl ether (2 x 50 mL). The aqueous layer was then acidified to pH=3 with IN HCl and then extracted with n-BuOH (5 x 100 mL). The organic layers from the n-BuOH extraction were combined and the solvent was evaporated under vacuum to give a residue which was purified by HPLC (40% ACN in water containing 0.05% TFA) to give the title compound. MS [M+H] found 371.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Chloroethyl)-1H-pyrazole, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FENG, Jun; KEUNG, Walter; LARDY, Matthew; WO2010/129848; (2010); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 4331-28-6,Some common heterocyclic compound, 4331-28-6, name is 1H-Pyrazol-4-amine hydrochloride, molecular formula is C3H6ClN3, 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 mixture of (S)-2-(methylcarbamoyl)-6-(1-phenylethyl)isonicotinic acid (80.5 mg, 0.28 mmol) and HATU (172.0 mg, 0.45 mmol) was added 1H-pyrazol-4-amine hydrochloride (51.6 mg, 0.43 mmol) and DMF (1.8 mL). DIPEA (0.173 mL, 0.99 mmol) was added and the mixture was stirred at rt for 2 h. The mixture was concentrated under a stream of nitrogen and diluted with acetonitrile to a total volume of 2 mL and directly purified by MDAP (2 x 1 mL injection; formic) and the required fractions (fraction 1 from both runs) were combined and evaporated in vacuo. The residue was redissolved inmethanol ( 6 mL) and transferred to a tarred vial, the solvent evaporated under a stream of nitrogen and the residue dried in vacuo to give the desired product as a yellow solid, (S)-N2-methyl-6-(1- phenylethyl)-N4-( 1 H-pyrazol-4-yl)pyridine-2,4-d icarboxamide (87.5 mg, 0.25 mmol, 88 % yield)LCMS (2 mm Formic): Rt = 0.91 mi [MH]+ = 350.3.1H NMR (400 MHz, DMSO-d6) O ppm 10.87 (5, 1 H) 8.80 (d, J=4.2 Hz, 1 H), 8.38 (5, 1 H) 7.80 – 7.96(m, 3 H), 7.43 (d, J=7.6 Hz, 2 H), 7.31 (t, J=7.2 Hz, 2 H), 7.13 – 7.25 (m, 1 H), 4.45 (q, J=6.6 Hz, 2 H), 2.91 (d, J=3.9 Hz, 3 H), 1.74 (d, J=6.8 Hz, 3 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Pyrazol-4-amine hydrochloride, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (N.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan, Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (0 pag.)WO2018/158210; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 537039-17-1, name is 5-(4-Methylpiperazin-1-yl)-1H-pyrazol-3-amine, 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. COA of Formula: C8H15N5

Step 5: A mixture of N-[3-(3-dimethylamino-acryloyl)-phenyl]-3-trifluoromethyl-benzamide (40 mg, 0.22 mmol) and 5-(4-Methyl-piperazin-1-yl)-2H-pyrazol-3-ylamine (37 mg, 0.20 mmol) in 2 mL of acetic acid is heated at 80 C. over night. Then the reaction mixture is concentrated and diluted with ethyl acetate. N-{3-[2-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl}-3-(trifluoromethyl)benzamide (67.3 mg, 70% yield) is obtained by reverse phase chromatography purification. HPLC: Rt=2.0 min; MS 481 [M+H]MS (electrospray): m/z 481.2 [M+H]

The synthetic route of 5-(4-Methylpiperazin-1-yl)-1H-pyrazol-3-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2007/219186; (2007); 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. 4331-28-6, name is 1H-Pyrazol-4-amine hydrochloride, A new synthetic method of this compound is introduced below., Computed Properties of C3H6ClN3

A solution of 5-(2-chloropyridin-4-yl)-2-cyclopropylmethoxybenzonitrile (0.25 g, 0.0878 mmol) in t-butanol (5 ml) is degassed with nitrogen for 5 min. 1H-Pyrazol-4-ylamine hydrochloride (0.12 g, 1.08 mmol), Josiphos (24.3 mg, 0.00439 mmol) and tris(dibenzylideneacetone)dipalladium(0) (40.0 mg, 0.00439 mmol) is then added. A solution of 1.6M lithium bis(trimethylsilyl)amide in THF (0.35 g, 2.1 mmol) is added dropwise. The mixture is irradiated in the microwave at 140 C. for 2 h. 30 ml of water are then added, and the mixture is filtered. The crude product is purified by chromatography, giving 26.6 mg of the desired product as brown solid; [0540] 1H NMR (400 MHz, DMSO-d6): delta [ppm] 12.47 (bs, 1H), 8.80 (s, 1H), 8.13 (d, J=5.36 Hz, 1H), 8.04 (d, J=2.16 Hz, 1H), 7.92 (dd, J=2.24, 8.82 Hz, 2H), 7.54 (bs, 1H), 7.34 (d, J=8.92 Hz, 1H), 6.92 (d, J=5.28 Hz, 1H), 6.86 (s, 1H), 4.06 (d, J=7.00 Hz, 2H), 1.23-1.30 (m, 1H), 0.59-0.63 (m, 2H), 0.31-0.39 (m, 2H); [0541] LCMS: (method A) 332 (M+H), RT. 3.25 min; [0542] HPLC: (method A) RT. 3.23 min.

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; MERCK PATENT GMBH; Hoelzemann, Guenter; Dorsch, Dieter; Eggenweiler, Hans-Michael; US2014/228340; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 709-04-6, name is 1-Phenyl-1H-pyrazole-4-carbonitrile, 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 709-04-6, category: pyrazoles-derivatives

To a solution of nitrile 1011(300 mg, 1.77 mmol) in TI-IF (3 mL) was added Ti(O4Pr)4 (0.6 mL, 194 mmoi) at room temperature. Grignard reagent (4.5 mL, 443 mmoi)was added to the reaction mixture dropwise under argon atmosphere at -78C and the reaction mixture was stirred at -78C for 0.5 h and then at ambient temperature for 1 h. To the above reaction mixture at room temperature BF3OEt2 (0.5 mL, 3.54 rnrnoi) was added and stirred for I it After completion of reaction, the reaction mixture was quenched with water (3.0 mL), 2M HCI (2.0 mL) up to pI-i:::3 and stirred for 15 miii and then basified with 6N NaOH up to pH:::iO.The reaction mixture was extracted with 10% CH2C12/MeOH (15 mE >< 3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was further purified by Combifiash column chromatography (CH?Cl2/I4eOH. 0 to 10%) to afford 1012 (60 mg, 1 7%) as an oil. MS (MM) miz 19g. I [M-4-H] -F. 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-Phenyl-1H-pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see. Reference:
Patent; IOMET PHARMA LTD.; MERCK SHARP & DOHME CORP.; COWLEY, Phillip, M.; HAN, Yongxin; (67 pag.)WO2017/48612; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 423768-52-9,Some common heterocyclic compound, 423768-52-9, name is 3-(Aminomethyl)-1,5-dimethylpyrazole, molecular formula is C6H11N3, 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.

Under argon, a solution of 3-chloro-5-(2,6-dimethoxyphenyl)-1,2,4-triazine (6.85 mg, 0.027 mmol, prepared as in example 41), (1,5-dimethyl-1H-pyrazol-3-yl)methylamine (8 mg, 0.064 mmol) and potassium carbonate (3.8 mg, 0.028 mmol) in anhydrous acetonitrile (0.7 mL) was stirred at 85C overnight. The solution was evaporated. The residue was purified by preparative TLC (silica gel, dichloromethane/methanol 95/5) to afford 5-(2,6-dimethoxyphenyl)-N-[(1,5-dimethyl-1H-pyrazol-3-yl)methyl]-1,2,4-triazin-3-amine (5.5 mg, 59%) as an off-white solid. ESI-MS m/z 341 (M+H)+. 1H NMR (CDCl3), delta (ppm): 8.45 (s, 1H), 7.40 (t, J = 8.4 Hz, 1H), 6.64 (d, J = 8.4 Hz, 2H), 6.06 (s, 1H), 4.70 (d, J = 5.2 Hz, 2H), 3.77 (s, 6H), 3.73 (s, 3H), 2.23 (s, 3H).

The synthetic route of 423768-52-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mutabilis; EP2141164; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 40711-33-9, 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. 40711-33-9, name is Ethyl 5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of ethyl 5-oxo-2,5-dihydro-1 H-pyrazole-3-carboxylate (0.6 g, 3.84 mmol, which may be prepared as described in Synthesis 2003, 15, 2353-2357), 1 ,1- dimethylethyl 4-hydroxy-1-piperidinecarboxylate (1.160 g, 5.76 mmol) and TPP (1.774 g, 6.76 mmol) in THF (8.4 ml), at 0 0C and under a nitrogen atmosphere, a solution of bis(1 ,1-dimethylethyl) (E)- 1 ,2-diazenedicarboxylate (DBAD) (1.59 g, 6.92 mmol) in THF (2.4 ml) was added. After 5 min the ice-bath was removed and the reaction mixture was stirred at RT. After 2h additional amount of 1 ,1-dimethylethyl 4-hydroxy-i-piperidinecarboxylate (150 mg), TPP (160 mg) and DBAD (140 mg) were added and the reaction mixture was stirred overnight. The reaction mixture was concentrated under vacuum and the residue was purified by FC on silica (eluting with Cy/EA from 1/0 to 7/3) to give 0.32 g of the title product .MS(m/z): 340.12 [MH]+.Following the above procedure, starting from ethyl 5-oxo-2,5-dihydro-1 H-pyrazole-3- carboxylate (0.8 g, 5.12 mmol) and 1 ,1-dimethylethyl 4-hydroxy-1-piperidinecarboxylate (1.65 g, 8.20 mmol) a further amount of the title compound (0.49 g) was prepared.MS(m/z): 340.12 [MH]+.

The chemical industry reduces the impact on the environment during synthesis Ethyl 5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/130232; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics