Day: May 21, 2021

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

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

Reference of 16082-33-0, A common heterocyclic compound, 16082-33-0, name is 1H-Pyrazole-3,5-diamine, molecular formula is C3H6N4, 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 1H-pyrazole-3,5-diamine (70 mg, 0.54 mmol) prepared by the procedure described in the literature (US82902, 2007) and pyridine (2.0 mL) was added III (100 mg, 0.20 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was concentrated to dryness under reduced pressure. The residue was purified by column chromatography (silica, 0-40% CMA in CH2Cl2) followed by preparative HPLC to afford the title compound (25 mg, 25%) as an off-white solid. [0527] Rf0.20 (180:18:2 Methylene Chloride/Methanol/concentrated Ammonium Hydroxide). 1H NMR (300 MHz, DMSO-d6) delta 0.83 (s, 3H), 0.92 (s, 3H), 0.95 (s, 3H), 1.0 (s, 3H), 1.25 (s, 6H), 1.30 (s, 3H), 1.30-1.90 (m, 23H), 2.06 (m, 3H), 2.25 (m, 1H), 2.44 (d, J = 15.0 Hz, 1H), 2.62 (m, 1H), 5.35 (s, 1H). mp >300C. APCI MS (Positive Mode) m/z 574 [C34H51N7O + H]+

The synthetic route of 16082-33-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sequoia Sciences, Inc.; Eldridge, Gary R.; Buckle, Ronald Neil; Ellis, Michael; Huang, Zhongping; Reilly, John Edward; EP2712863; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 35715-72-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 35715-72-1 name is 4-(Chloromethyl)-1-(2-fluorophenyl)-1H-pyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a mixture of 237 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (Preparation 71, 20 g, 71.7 mmol) in 21 DMF (200 mL) was added 116 K2CO3 (49.5 g, 358.5 mmol) and the mixture stirred for 10 min at rt before 239 4-(chloromethyl)-1-(2-fluorophenyl)-1H-pyrazole (Preparation 98, 20 g, 95.2 mmol) was added. The resulting mixture was stirred at 60 C. for 6 hr, filtered and concentrated under reduced pressure to give a crude product which was washed with EtOAc and water to afford the 197 title compound (20 g, 62.5%) as a yellow solid. 1HNMR (400 MHz, CDCl3): 5.41 (s, 2H), 7.20-7.32 (m, 3H), 7.42 (s, 1H), 7.72 (s, 1H), 7.84-7.87 (m, 1H), 8.05 (d, 1H), 8.68 (s, 1H). LCMS m/z=453.9 [MH]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Chloromethyl)-1-(2-fluorophenyl)-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; CYSTIC FIBROSIS FOUNDATION THERAPEUTICS, INC.; Strohbach, Joseph Walter; Limburg, David Christopher; Mathias, John Paul; Thorarensen, Atli; Denny, Rajiah Aldrin; Zapf, Christoph Wolfgang; Elbaum, Daniel; Gavrin, Lori Krim; Efremov, Ivan Viktorovich; (159 pag.)US2018/141954; (2018); 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

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

Synthetic Route of 50877-41-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 50877-41-3 name is 1-Benzyl-4-bromo-1H-pyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Preparation of Compound 4003, 3-{5-(1-ben2yl-1M-pyrazol-4-yl}-1W-indol-1-yl}-iV}W- dimethylpropan-1 -amine 1-Ben2y-4-bromo-1 H-pyrazole (237 mg, 1.0 mmol), 1-{3-(dimethylamino)propyl)-1H~ indoi-5-ylboronic acid (180 mg, 0,73 mmol) and Na2C03 (315 mg, 3.0 mmol) were dissolved in a mixture of DMF (8 mL), EtOH (2 mL) and water (2 mL). Pd(PPh3)4 (115 mg, 0,1 mmol) was added under a nitrogen atmosphere and the mixture was heated at 100 C for 2 hours. Water (40 mL) was added and the resulting precipitate was collected, redissolved in EtOAc, dried over Na2S0 , and concentrated. The residue was purified by column chromatography (silica gel, D-GM:MeQH=15:1 ), followed b prep- TLC to afford the product (11 mg, 4%). 1H NMR (400 MHz, CDCI3): delta 7.84 (s, 1H), 7.71 (s, 1 H), 7.62 (s, 1 H), 7,36-7.26 (m, 7H), 7,10 (d, J ~ 3.2 Hz, 1 H), 6.46 (d, J ~ 2.8 Hz, 1H), 5.35 (s, 2HJ, 4.19 (t, J – 7.0 Hz, 2H), 2.23-2.20 (m, 8H), 2.00-1.98 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Benzyl-4-bromo-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; NOVOGEN LTD; JAMES, Ian; DIXON, Ian; FEUTRILL, John; CUZZUPE, Anthony; TREUTLEIN, Herbert; ZENG, Jun; NERO, Tracy; WO2015/74123; (2015); 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

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

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