Tag: M.W:100-200

Reference of 299930-70-4, A common heterocyclic compound, 299930-70-4, name is 3-Chloro-1-methyl-4-nitro-1H-pyrazole, molecular formula is C4H4ClN3O2, 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.

Step 2: Into a 100 mL round bottom flask containing a solution of 3-chloro-l-methyl-4-nitro- lH-pyrazole (2.0 g) in ethyl acetate (50 mL) was added Raney Ni (1.0 g) and the reaction mixture was stirred under hydrogen atmosphere for 24 h. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and purified by flash chromatography eluting with ethyl acetate in petroleum ether (40- 50%) to afford 3 -chloro-1 -methyl-1H-pyrazol-4-amine as an oil. *H NMR (CD3OD, 400 MHz): 5 7.17 (s, 1H), 3.73 (s, 3H).

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.; LIM, Jongwon; ALTMAN, Michael, D.; GIBEAU, Craig, R.; (84 pag.)WO2016/144849; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 37622-90-5, These common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, 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.

Reference Example 1 ethyl 3,5-dibromo-1H-pyrazole-4-carboxylate (0885) (0886) To a mixed solution of ethyl 1H-pyrazole-4-carboxylate (31.0 g), sodium acetate (118 g), ethanol (200 mL) and water (300 mL) was added bromine (141 g), and the mixture was stirred at room temperature for 10 hr. To the reaction mixture was added sodium thiosulfate (175 g), and the solvent was evaporated under reduced pressure. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (65.1 g). MS (ESI+): [M+H]+ 296.7

Statistics shows that Ethyl 4-pyrazolecarboxylate is playing an increasingly important role. we look forward to future research findings about 37622-90-5.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
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, name: 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine

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

Application of 114474-28-1, 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 114474-28-1 as follows.

A mixture of 4-(lH-pyrazol-4-yl)aniline (120 mg, 0.75 mmol), 2,4-dichloro- 7-fluoroquinazoline (164 mg, 0.75 mmol), and zPrNEt2 (195 mg, 1.51 mmol) in DMF (2.51 mL) was stirred at 90 C overnight, cooled to rt, diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (245 mg, 96%). MS (ES+) m/e 340 (M+H)+.

According to the analysis of related databases, 114474-28-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KADMON CORPORATION, LLC; KIM, Ji-ln; OLSZEWSKI, Kellen, L.; BARSOTTI, Anthony, M.; POYUROVSKY, Masha, V.; LIU, Kevin, G.; MORRIS, Koi; YU, Xuemei; (129 pag.)WO2018/201006; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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

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, Product Details of 5334-40-7

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

Related Products of 37687-18-6, The chemical industry reduces the impact on the environment during synthesis 37687-18-6, name is 1-(1-Methyl-1h-pyrazol-4-yl)-ethanone, I believe this compound will play a more active role in future production and life.

Method 31 Synthesis of 2-bromo-1-(6-methyl-3-pyridyl)ethanone (Intermediate 45) To a solution of R-12 (10 g, 79.3 mmol) in MeCN (200 mL) at 0 C. is added N,O-dimethylhydroxylaminehydrochloride (8.5 g, 87.2 mmol), EDCI (18.2 g, 95.2 mmol), 1-hydroxybenzotriazole (3.2 g, 23.8 mmol) followed by triethylamine (20.5 mL, 158 mmol) and stirred at room temperature 15 h. The reaction mixture is partitioned between water and EtOAc. The collected organics are dried with anhydrous Na2SO4, filtered, and concentrated in vacuo to give I-43 (12 g) m/z 170.0 [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, 1-(1-Methyl-1h-pyrazol-4-yl)-ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BARTOLOZZI, Alessandra; CHEN, Zhidong; DINES, Jonathon Alan; LO, Ho Yin; LOKE, Pui Leng; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee M.; US2013/196967; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 82560-12-1,Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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-1H-pyrazol-5-amine (J-III) (1 eq., 40 g) was dissolved in dilute HCI (120 ml of HCI in 120 ml of water) and mixed dropwise with NaNO2 (1.03 eq., 25 g in 100 ml) at 0 – 5 0C over a period of 30 min. After stirring for 30 minutes, the reaction mixture was neutralised with Na2CO3. A diazonium salt obtained by reaction of KCN (2.4 eq., 48 g), water (120 ml) and CuCN (1.12 eq., 31 g) was added dropwise to the reaction mixture within 30 min and the mixture was stirred for a further 30 min at 75 0C. After complete reaction, the reaction mixture was extracted with EE (3 x 500 ml), the combined organic phases were dried over sodium sulphate and the solvent was removed under vacuum. The purification (SiO2, 20 % EE/hexane) of the residue by column chromatography produced a white solid (J-IV) (6.5 g, 15.1 % yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-5-tert-butylpyrazole, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; SCHIENE, Klaus; DE VRY, Jean; DAMANN, Nils; FRORMANN, Sven; LESCH, Bernhard; LEE, Jeewoo; KIM, Yong-Soo; KIM, Myeon-Seop; WO2010/127856; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 34334-96-8 as follows. Computed Properties of C4H5N3O2

General procedure: Bromo-3-methoxypropane (1.20 mL, 10.51 mmol) was added at rt to a mixture of 5 – nitro-lH-pyrazole (1.00 g, 8.84 mmol), K2C03 (2.35 g, 17.00 mmol) in DMF (10 mL). This reaction was stirred in a sealed tube at 120 C using one single mode microwave (Biotage Initiator EXP 60) with a power output ranging from 0 to 400 W for 30 min. Then, water was added and this mixture was extracted twice with EtOAc. The organic layers were mixed, dried over MgS04, filtered and the solvent was evaporated until dryness. The residue was purified by column chromatography on silica gel (Irregular SiOH, 40 muiotaeta, 80 g, mobile phase: gradient from 70% heptane, 29% EtOAc, 1% MeOH (+10% NH4OH) to 40% heptane, 52% EtOAc, 8% MeOH (+10% NH4OH)). The pure fractions were collected and the solvent was evaporated until dryness to give 1.39 g of intermediate 56 (85% yield) and 267 mg of intermediate 56′ (16% yield). These intermediates were used as it in the next step

According to the analysis of related databases, 34334-96-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (472 pag.)WO2018/2217; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 15802-80-9, name is 3-(tert-Butyl)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 15802-80-9, Product Details of 15802-80-9

Reference Production Example 3-2 3-t-butyl-1H-pyrazole-1-ylmethanol The mixture of 1.28 g of 3-t-butyl-1H-pyrazole, 0.66 g of paraformaldehyde and 0.3 g of triethylamine was stirred at 130 C for 7 hours. After the reaction mixture was cooled to room temperature, acetone was added to the reaction mixture. The mixture was filtered. The filterate was concentrated under reduced pressure. Hexane was added to the residue, and then crystalline was formed. The crystalline was collected to obtain 1.07 g of 3-t-butyl-1H-pyrazole-1-ylmethanol. 1H-NMR(CDCl3,TMS,delta(ppm)):1.28(9H,s),5.50(2H,s),6.13(1H,s),7.46 (1H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(tert-Butyl)pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP1710234; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics