Tag: M.W:100-200

Electric Literature of 3469-69-0,Some common heterocyclic compound, 3469-69-0, name is 4-Iodopyrazole, molecular formula is C3H3IN2, 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 1 In a flask were combined 4-iodo-1H-pyrazole (1.00 g, 5.16 mmol), cyclopropylboronic acid (886 mg, 10.3 mmol) and sodium carbonate (1.09 g, 10.3 mmol) and the mixture suspended in 1,2-dichloroethane (20 mL). A suspension of copper (II) acetate (936 mg, 5.16 mmol) and 2,2-bipyridine (805 mg, 5.16 mmol) in 1,2-dichloroethane (40 mL) was warmed to 50 C. and added and the resulting mixture heated at 70 C. overnight. The mixture was then cooled and filtered and the solids rinsed with EtOAc. The combined filtrates were concentrated and the residue taken up in EtOAc and 50% saturated aqueous NH4Cl. The organic layer was washed with sat NH4Cl, sat NaHCO3 and sat NaCl and dried over MgSO4. The solution was concentrated and the residue purified by SiO2 chromatography (5-35% EtOAc/heptane) to afford 517 mg (43%) 1-cyclopropyl-4-iodo-1H-pyrazole as a colorless oil.

The synthetic route of 3469-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); 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. 118430-73-2, name is 3-(tert-Butyl)-1-methyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., SDS of cas: 118430-73-2

5-Amino-3-tert-butyl-1-methylpyrazole (1.32 g) was added to a stirred solution of phenyl {3- [ (2-chloropyrimidin-5-yl) ethynyl] phenyl} carbamate (Intermediate 35) (2.0 g) in THF (120 mL) and triethylamine (1.2 mL) and the reaction mixture was heated at 65C for 8 hours. The solvent was evaporated and the residue was triturated with ether/DCM to give the title compound as an off-white solid (1.5 g, 64%); MS m/e MHF 409.

The synthetic route of 118430-73-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/60970; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 55864-87-4, These common heterocyclic compound, 55864-87-4, name is Ethyl 4-nitro-1H-pyrazole-3-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.

A mixture of 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester (6.40 g, 34.6 mmol) and 10% Pd/C (650 mg) in EtOH (150ml) was stirred under an atmosphere of hydrogen for 20 h. The mixture was filtered through a plug of Celite, reduced in vacuo and dried through azeotrope with toluene to afford 4-amino-1H-pyrazole-3- carboxylic acid ethyl ester as a pink solid (5.28 g, 98%). (1H NMR (400 MHz1 DMSO-d6) D 12.7 (s, 1 H), 7.1 (s, 1 H), 4.8 (s, 2H), 4.3 (q, 2H), 1.3 (t, 3H)).

The synthetic route of 55864-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77424; (2006); A1;; ; Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77425; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 2075-46-9,Some common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

Step2:[00394] To a stirred mixture of iron (1.68g, 30 mmol), ammonium chloride (540mg, 10 mmol), water (2ml_) and ethanol (8ml_) at 800C was added 4-nitro-1 H-pyrazol (1 .13g, lOmmol) in portions. After completion of addition, the mixture was stirred at 800C for additional 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate, and the resultant mixture was filtered through a pad of celite. The filtrate was concentrated to afford the crude title compound which was used at next step without further purification. MS (ES) [M+H]+ expected 84.0, found 84.0.

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

Reference:
Patent; CHEMOCENTRYX, INC.; WO2008/8375; (2008); A2;,
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 42027-81-6 as follows. HPLC of Formula: C5H7N3O3

A 100 mL round-bottom flask was charged with a solution of intermediate 28.2 (500 mg, 3.18 mmol, 1.00 equiv) in methanol (20 mL) and palladium on carbon (100 mg). To the above hydrogen gas was introduced. The resulting solution was stirred for 2 h at room temperature. The solids were filtered out and mixture was concentrated under vacuum to provide 350 mg (crude) of intermediate 28.3 as yellow oil. LCMS (ES, m/z): 128 [M+H].

According to the analysis of related databases, 42027-81-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); 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

Synthetic Route 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

Application 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

Electric Literature 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

Synthetic Route 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