Day: September 17, 2021

Related Products of 13808-64-5, 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. 13808-64-5, name is 4-Bromo-3-methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows.

PREPARATIVE EXAMPLE 15; Step A; N-methyl-4-bromopyrazole-3-carboxylic acid was prepared according to known methods, see: Yu. A. M.; Andreeva, M. A.; Perevalov, V. P.; Stepanov, V. I. ; Dubrovskaya, V. A.; and Seraya, V. l. in Zh. Obs. Khim, (Journal of General Chemistry of the USSR) 1982,52, 2592 (and the references cited therein) the disclosure of whichis incorporated hereinby reference thereto.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3-methylpyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2005/66147; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5334-39-4, 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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of PPh3 (4.28 g, 0.016 mole, 1.1 equiv) and DIAD (3.33 gm,, 0.016 mole, 1.1 equiv) in THF (2mL), was added 4-nitro-lH-pyrazole (1.96 g, 0.004 mmol, 1.0 equiv) The reaction mixture was added l-[2, 4-bis (trifluoromethyl) phenyl] ethanol (4 g, 0.004 mmol, 1.0 equiv). The reaction mixture was stirred at room temperature for 1 hrs. Product formation was confirmed with TLC and LCMS. After completion of reaction mixture were diluted with EtOAc (50 mL) and washed with water (3×50 mL). Organic layer dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain crude which was further purified by flash column chromatography to obtain pure product l-(l-(2,4- bis(trifluoromethyl)phenyl)ethyl)-5-methyl-4-nitro-lH-pyrazole (0.5 gm) and l-(l-(2,4- bis(trifluoromethyl)phenyl)ethyl)-3-methyl-4-nitro-lH-pyrazole (1.5 gm). LCMS: 368 [M+H] +.

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, 3-Methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRAXIS BIOTECH LLC; ALFARO, Jennifer; BELMAR, Sebastian; NUNEZ VASQUEZ, Gonzalo Esteban; PUJALA, Brahmam; SATHE, Balaji Dashrath; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; THAKRAL, Pooja; PATIDAR, Rajesh Kumar; (344 pag.)WO2019/195810; (2019); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 42098-25-9, These common heterocyclic compound, 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, 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.

tert-Butyl 8-(1-methyl-4-nitro-1H-pyrazol-5-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate A mixture of 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 (150 mg, 0.93 mmol), tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (244 mg, 1.02 mmol) and DIPEA (1 mL) in EtOH (3 mL) was heated at 130 C. in a microwave for 2 hr. The solvent was removed under reduced pressure and the crude product was purified via silica gel column chromatography (50% EtOAc/isohexane) to give tert-butyl 8-(1-methyl-4-nitro-1H-pyrazol-5-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate as a yellow oil (245 mg, 72%). 1H NMR (400 MHz, CDCl3) delta 8.02 (s, 1H), 3.76 (s, 3H), 3.49-3.39 (m, 2H), 3.30-3.00 (m, 6H), 1.90-1.60 (m, 6H), 1.55 (s, 9H).

Statistics shows that 5-Chloro-1-methyl-4-nitro-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 42098-25-9.

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5334-40-7, name is 4-Nitro-1H-pyrazole-3-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 5334-40-7, COA of Formula: C4H3N3O4

Step 1. 4-Nitro-lH-pyrazole-3-carboxylic acid ethyl ester; Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 hours. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-lH-pyrazole-3- carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (1H NMR (400 MHz, DMSO-d6) delta 14.4 (s, IH), 9.0 (s, IH), 4.4 (q, 2H), 1.3 (t, 3H)).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Nitro-1H-pyrazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; NOVARTIS AG; WO2008/7123; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 133261-11-7, These common heterocyclic compound, 133261-11-7, name is Ethyl 3-cyclopropyl-1-methyl-1H-pyrazole-5-carboxylate, 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.

General procedure: 2a (0.05 mol) was added to a stirred mixture of NaOH (6.0 g, 0.15 mol) and water (100 mL). After 4 h under 80 C, the mixture was poured into ice water and the pH was adjusted to acidic. Then 10 % HCl was slowly added to the solutions until a large amount of solids precipitated. After filtration, the solids were dried; 4.6 g (92 % purity) white solid (3a) was obtained. Yield 60 %; GC-MS (EI, 70Ev) (m/z 140 (M+). 3b-p were synthesized in a similar procedure.

Statistics shows that Ethyl 3-cyclopropyl-1-methyl-1H-pyrazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 133261-11-7.

Reference:
Article; Huang, Danling; Huang, Mingzhi; Liu, Weidong; Liu, Aiping; Liu, Xingping; Chen, Xiaoyang; Pei, Hui; Sun, Jiong; Yin, Dulin; Wang, Xiaoguang; Chemical Papers; vol. 71; 11; (2017); p. 2053 – 2061;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 127107-23-7, 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. 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

In a pressure tube, l-methylpyrazol-4-amine HCI (21 mg, 0.16 mmol), (S,2S)-2-(6-((2- bromo pyridin-4-yl)methoxy)-4-methoxybenzo[cf|thiazol-2-ylamino) cyclohexanol (60 mg, 0.13 mmol), RuPhos Pd G4 (11 mg, 0.013 mmol), RuPhos (6 mg, 0.013 mmol) and Cs2C03 (127 mg, 0.39 mmol) were dissolved in 1,4-dioxane (2 mL). The tube was sealed and purged with N2. The reaction mixture was stirred at 85C for 3h. LCMS monitored the reaction. The mixture was filtered and purified by mass-triggered preparative HPLC (Mobile phase: A = 10M NH4HCO3/H2O, B = MeCN; Gradient: B = 30-60%; 10.0 min; Column: C18) to give (15′,25)-2-(4-methoxy-6-((2-(l-methyl-lH-pyrazol-4-ylamino)pyridin-4-yl) (1492) methoxy)benzo[cf|thiazol-2-ylamino)cyclohexanol (5 mg, 9%) as a white solid. MS (ES+) C24H28N603S requires: 480, found: 481 [M+H]+. NMR (500MHz, DMSO) delta 8.81 (s, 1H), 8.07 (d, J = 5.3 Hz, 1H), 7.91 (s, 1H), 7.61 (d, J = 7.5 Hz, 1H), 7.37 (s, 1H), 6.91 (d, J = 2.3 Hz, 1H), 6.70 (s, 1H), 6.65 (d, J= 5.3 Hz, 1H), 6.54 (d, J = 2.2 Hz, 1H), 5.02 (s, 2H), 4.77 (d, J = 5.0 Hz, 1H), 3.83 (s, 3H), 3.79 (s, 3H), 3.51 (s, 1H), 2.02 (s, 1H), 1.87 (d, J = 11.2 Hz, 1H), 1.63 (t, J= 10.8 Hz, 2H), 1.23 (s, 5H).

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-pyrazol-4-amine hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TESARO, INC.; JONES, Philip; CZAKO, Barbara; BURKE, Jason P.; CROSS, Jason; LEONARD, Paul Graham; TREMBLAY, Martin; MANDAL, Pijus; (232 pag.)WO2018/119387; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 31230-17-8,Some common heterocyclic compound, 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

A mixture of compound C (1.0 g, 2.94 mmol)and 3-amino-5- methylpyrazole (314 mg, 3.23 mmol) in dimethylformamide (6 ml) was treated with diisopropylethylamine (0.614 ml, 3.53 mmol) and sodium iodide (530 mg, 3.53 mmol). The mixture was stirred under nitrogen at 85 ° for 4 hours, cooled to room temperature and diluted with ethyl acetate. The solution was washed with water (x 4), dried over magnesium sulphate and concentrated to 5 ml to afford, upon crystallization and harvesting of colourless crystals, the title compound D (920 mg, 78percent). 1H-NMR DMSO-d6, delta 0.80-0.87 (4H, m), 1.77-1.85 (IH, m), 1.92 (IH, s), 5.24 (IH, br s), 6.47 (IH, br s), 7.55 (2H, d), 7.70-7.80 (2H, m), 10.24 (IH, s), 10.47 (IH, s), 11.92 (IH, s).

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

Reference:
Patent; MERCK & CO., INC.; WO2008/13807; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C5H6N2O, 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: C5H6N2O

Preparation 65: 3 ‘-Chloro-4-( 1 -methyl- 1 H-pyrazol-4-ylmethyl)-3 ,4,5 ,6-tetrahydro-2H- [l,2′]bipyrazineDissolve 3′-chloro-3,4,5,6-tetrahydro-2H-[l,2’]bipyrazinyl (3.43 g, 17.3 mmol) in tetrahydrofuran (100 mL). Add 1 -methyl- lH-pyrazole-4-carbaldehyde (2.244 g, 20.38 mmol) in dry tetrahydrofuran (5 mL), stir for 10 min. at room temperature, add sodium triacetoxyborohydride (4.32 g, 20.4 mmol) and subject the reaction to ultrasound stirring for 6 hr. at room temperature. Add saturated aqueous sodium hydrogen carbonate (100 mL) then 2 N sodium hydroxide (10 mL) to the mixture and extract with DCM (2 x 200 mL). Pass the combined DCM extracts through an 1ST Phase Separator Frit, concentrate and purify (silica gel chromatography, eluting with 0: 100 to 8:92 methanol:DCM), to give the title preparation as a crystalline solid (5.21 g, 92%). MS (ES): m/z = 293.1 [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 25016-11-9, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/141020; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 86477-09-0, name is Ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate, 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. Product Details of 86477-09-0

Add 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid ethyl ester (3.10 g, 17.2 mmol) and 30 mL of water to a 100 mL vial and cool to 0 C.Add sodium hydroxide solid (4.8 g, 86.0 mmol), stir to dissolve,Transfer to room temperature for 3 h, TLC detection reaction is completed,Wash once with 30 mL of DCM, adjust the pH of the aqueous phase to about 5 with concentrated hydrochloric acid.A white solid is precipitated and suction filtered to obtain a part of the product.The filtrate was extracted 3 times with 50 mL of EA, and the organic phases were combined and dried over anhydrous sodium sulfate.Filtered, concentrated,A total of 1.7g of light yellow solid, a yield of 65%,

The synthetic route of Ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Lin Xinglong; Xie Hongming; Hu Yangxiao; Li Shiguang; Zhang Yingjun; Tan Yumei; Yuan Mingyun; (124 pag.)CN108948019; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 118430-74-3, name is 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine, 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 118430-74-3, SDS of cas: 118430-74-3

Synthesis of N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-((methylsulfonyl)methyl)-9H-pyrimido[4,5-b]indol-4-amine (Cpd. No. 289) Pd2(dba)3 (18 mg) and BINAP (26 mg) were mixed in anhydrous toluene. And the mixture was heated at reflux for 3-4 minutes. This mixture was transferred into a round-bottom flask containing ZBB273 (60 mg), 3-cyclopropyl-1-methyl-1H-pyrazol-5-amine (84 mg), K3PO4 (130 mg), and toluene (4 mL). The mixture was heated at reflux for overnight before quenching with methanol. The reaction mixture was filtered and the mixture was purified by HPLC to yield Cpd. No. 289 as a CF3CO2H salt in 27 mg. ESI-MS calculated for C25H28N7O4S [M+H]+=522.19; Observed: 522.44.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Zhao, Yujun; Zhou, Bing; Aguilar, Angelo; Liu, Liu; Bai, Longchuan; McEachern, Donna; Sun, Duxin; Wen, Bo; Luo, Ruijuan; Zhao, Ting; Chinnaiyan, Arul; Asangani, Irfan A.; Stuckey, Jeanne; Meagher, Jennifer Lynn; Ran, Xu; US2015/246923; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics