Day: August 16, 2021

Reference of 1904-31-0,Some common heterocyclic compound, 1904-31-0, name is 1-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.

2-Bromo-5-fluoropyridine (1) (1 .Og, 5.71 mmol), i-methyl-i H-pyrazol-3-amine (2) (554mg, 5.7immol), Xantphos (0.330g, 0.S7mmol), and 0s2003 (2.79g, 8.S6mmol) were combined in dry i,4-dioxane (i5mL). The reaction mixture was degassed with N2(g) and placed under vacuum for 10mm. Pd2(dba)3 (0.26ig, 0.28mmol) was then added and the resulting reaction mixture was heated at 9000 for 30h. It was then poured onto demineralized water (200mL), and extracted with EtOAc (3 x iOOmL). The organic phases were combined, dried over Na2SO4, filtered and subsequently concentrated in vacuo. The resulting residue was purified by flash chromatographywith EtOAc/Hexane (1:1) to provide 5-fluoro-N-(i -methyl-i H-pyrazol-3-yl)pyridin-2- amine (3) as a yellow solid (0.65g, 6ipercent).LCMS (ES): Found i93.0 [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 1-Methyl-1H-pyrazol-3-amine, its application will become more common.

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; TOMASSI, Cyrille Davy; CECIL, Alexander Richard Liam; MACCORMICK, Somhairle; NODES, William John; SILVA, Franck Alexandre; WO2014/181137; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 26621-44-3, name is 3-Nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C3H3N3O2

To a solution of 3-nitro-1H-pyrazole (3.16 g, 28 mmol) in acetic acid (50 mL) at 0 C was added dropwise fuming HNO3 (2.6 mE, c.a. 58 mmol). Acetic anhydride (6.6 mL, 70 mmcd) was added and the mixture was stirred at it for 3h. The mixture was cooled to 0 C and another portion of fuming HNO3 (0.5 mL, c.a. 11 mmol) was added and the mixture was stirred at it for 2h. The mixture was poured into water, stirred at it overnight, and extracted with EtOAc. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 10% EtOAc in petroleum ether to afford 1,3-dinitro-1JJ-pyrazole as a white solid(3.56 g, 81%).

The synthetic route of 26621-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PLEXXIKON INC.; HOLLADAY, Mark W.; LIU, Gang; (267 pag.)WO2017/19804; (2017); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25016-20-0, name is 1-Methyl-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 25016-20-0, COA of Formula: C5H6N2O2

Example 34 1-Methyl-N-4-[rel-(4aS,5aR)-5a-methyl-4,6-dioxo-3-(phenylamino)-1 ,4,4a,5,5a,6- hexah drocyclopropa[f]indol-2-yl]pyridin-2-yl-1 H-pyrazole-3-carboxamide A solution of 1 -methyl-1 H-pyrazole-3-carboxylic acid (1 10 mg, 871 muiotaetaomicronIota) and HATU (331 mg, 871 muiotaetaomicronIota) in DMA (3 mL) was added to a mixture of rel-(4aR,5aR)-2-(2-Aminopyridin- 4-yl)-3-anilino-5a-methyl-4a,5,5a,6-tetrahydrocyclopropa[f]indol-4(1 H)-one (26; 100 mg, 290 muiotaetaomicronIota) and DIPEA (152 muIota_, 871 muiotaetaomicronIota) in DMA (3 mL) and stirred for 16 h at 50 under an atmosphere of air. The mixture was concentrated, DCM added and washed with water and dried over sodium sulfate. After filtration and concentration the residue was purified by Biotage (SNAP NH 28 g, EtOH:DCM) to give the title compound (27 mg, 19%). 1 H-NMR (400 MHz, DMSO-de), delta [ppm]= 1 .39 (3H), 1 .58 (1 H), 1 .85 (1 H), 2.32 (1 H), 3.96 (3H), 6.53-6.61 (3H), 6.85 (1 H), 7.00 (2H), 7.38 (1 H), 7.50 (1 H), 7.88 (1 H), 8.23 (1 H), 8.52 (1 H), 9.51 (1 H), 13.13 (1 H)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GRAHAM, Keith; KLAR, Ulrich; BRIEM, Hans; SIEMEISTER, Gerhard; MOeNNING, Ursula; (145 pag.)WO2017/21348; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 930-36-9, name is 1-Methylpyrazole, 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 930-36-9, Computed Properties of C4H6N2

Two identical reactions were carried out in parallel.To a mixture of 1 -methylpyrazole (750 g, 9.16 mol) and acetic anhydride (1.7 kg, 16.67 mol) was added concentrated H2S04 (75 g, 0.75 mol) at about 20 C. The reaction mixture was heated at about 150 C. for about 3 hrs. After cooling, the two mixtures were combined, poured into ice-water (15 L), adjusted to about pH 10 with 20% aq. NaOH and extracted with DCM (4×10 L). The combined DCM extracts were dried (Na2SO4) and concentrated to afford the title compound as a brown oil (1240 g, 72%).?H NMR (400 MHz, CDCl3) delta: 7.86 (s, 1H), 7.84 (s, 1H), 3.92 (s, 3H), 2.40 (s, 3H).GCMS mlz=109.0 [M-CH3]+

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Pfizer Inc.; BROWN, Matthew Frank; DERMENCI, Alpay; FENSOME, Andrew; GERSTENBERGER, Brian Stephen; HAYWARD, Matthew Merrill; OWEN, Dafydd Rhys; WRIGHT, Stephen Wayne; XING, Li Huang; YANG, Xiaojing; (67 pag.)US2017/240552; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 10250-64-3, The chemical industry reduces the impact on the environment during synthesis 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, I believe this compound will play a more active role in future production and life.

To a stirred suspension of l-methyl-3-phenyl-lH-pyrazole-5-carboxylic acid (46 mg, CAS 10250-64-3) in dichloro ethane (2 ml) were added oxalyl chloride (44 mu) and DMF (2 drops). The reaction mixture was stirred at room temperature for 1 h and was then concentrated in vacuo. The residue was dissolved in THF (1 ml) and the resulting solution was added drop wise to a stirred solution of (+)-(R)-2-(4-amino-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (50 mg, example lh) and triethylamine (118 mu) in THF (2 ml). The reaction mixture was stirred at room temperature for 2 h. The crude reaction mixture was then concentrated in vacuo and the residue was purified by column chromatography (Si02; gradient: 0 % to 50 % EtOAc in heptane) to give (R)-2-{3-fluoro-4-[(2-methyl-5-phenyl-2H-pyrazole-3-carbonyl)-amino]- phenyl}-morpholine-4-carboxylic acid tert-butyl ester (81 mg, quant.) as a white solid. MS (ISP): 503.1 ([M+Na]+), 481.3 ([M+H]+), 425.2 ([M+H-C4H8]+).

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-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GALLEY, Guido; NORCROSS, Roger; PFLIEGER, Philippe; WO2012/168265; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 139756-02-8,Some common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, molecular formula is C8H14N4O, 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: A mixture of 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 1a (1.0 mmol), Ketones 2(1.0 mmol) and InCl3 (10 mol%,) in acetonitrile (6 mL) was stirred at room temperature for the time indicated in Table 3. After completion of the reaction (indicated by TLC) the reaction mixture was filtered and wash with acetonitrile (2 X 5 mL) to remove the insoluble catalyst. The filtrate was collected and concentrated under vacuum. The solid isolated was triturated with MTBE (10 mL), filtered and dried to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, its application will become more common.

Reference:
Article; Ismail; Kuthati, Bhaskar; Thalari, Gangadhar; Bommarapu, Venkatesham; Mulakayala, Chaitanya; Chitta, Suresh Kumar; Mulakayala, Naveen; Bioorganic and Medicinal Chemistry Letters; vol. 27; 6; (2017); p. 1446 – 1450;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 180207-57-2, 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. 180207-57-2 name is 2-(1H-Pyrazol-4-yl)ethanol, 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.

REFERENCE EXAMPLE 3 2-(1-Triphenylmethyl-3-pyrazolyl)ethanol, and 2-(1-triphenylmethyl-4-pyrazolyl)ethanol A mixture of 2-(3-pyrazolyl)ethanol and 2-(4-pyrazolyl)ethanol (2.4:1) (2.50 g) was dissolved in DMF (30 ml). To the solution were added, while stirring, triethylamine (2.26 g) and trityl chloride (6.22 g). The mixture was stirred at 25 C. for one hour, then at 40 C. for one hour. The reaction mixture was diluted with water, which was subjected to extraction with ethyl acetate. The organic layer was washed with an aqueous saline solution, which was dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The concentrate was purified by means of a column chromatography (carrier: silica gel, 300 g, developing solvent: ethyl acetate-hexane, 1:1) to afford 2-(1-triphenylmethyl-3-pyrazolyl)ethanol (3.75 g) and 2-(1-triphenylmethyl-4-pyrazolyl)ethanol (1.42 g).

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6174877; (2001); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 37687-18-6, name is 1-(1-Methyl-1h-pyrazol-4-yl)-ethanone belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C6H8N2O

General procedure: Selenium dioxide (8.0 g, 0.072 mol) was dissolved in 50 mL 1,4-dioxane by warming to 50 oC. Compound 53c (16.2 g, 0.072 mol) was added to the resulting solution, and the reaction mixture was heated under reflux for 5 h. The reaction mixture was filtered, and the filtrate was concentrated. The residue was dissolved in 100 mL DCM, triethyl orthoformate (21.5 g, 0.145 mol) and p-toluene sulfonic acid monohydrate (0.3 g, 0.002 mol) were added, and the resulting mixture was heated under reflux for 1 h and concentrated. The residue was purified by silica gel chromatography (DCM)

The synthetic route of 37687-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhan, Zhengsheng; Peng, Xia; Liu, Qiufeng; Chen, Fang; Ji, Yinchun; Yao, Shanyan; Xi, Yong; Lin, Yipeng; Chen, Tiantian; Xu, Yechun; Ai, Jing; Geng, Meiyu; Duan, Wenhu; European Journal of Medicinal Chemistry; vol. 116; (2016); p. 239 – 251;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1254717-53-7, name is (5-(Trifluoromethyl)-1H-pyrazol-3-yl)methanamine, molecular formula is C5H6F3N3, 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. Recommanded Product: (5-(Trifluoromethyl)-1H-pyrazol-3-yl)methanamine

Step 11 :To a stirred solution of compound 11 (2.8 g, 13.9 mmol) in DCM (76 mL) was added TEA (7 mL, 41 .7mmol, 3.0 eq) followed by phenyl 3-fluoro-4-(hydroxymethyl)phenyl-carbamate (3.63 g, 31 .9mmol, 1 .0 eq.) (synthesis described for in example A58) at room temperature and the mixture was stirred for 16 h. After completion of the reaction, a solid precipitate was filtered and washed with DCM (2 mL) followed by n-pentane (5 mL) and dried to get 12 (3.38 g, 73 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1254717-53-7, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; SCHIENE, Klaus; DE VRY, Jean; DAMANN, Nils; LESCH, Bernhard; BAHRENBERG, Gregor; SAUNDERS, Derek John; STOCKHAUSEN, Hannelore; KIM, Yong-Soo; KIM, Myeong-Seop; LEE, Jeewoo; WO2013/68461; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 25016-11-9, 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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

1-Methyl-1H-pyrazole-4-carbaldehyde (11.0 g, 0.1 mol), sodium bromate (6.0 g, 0.04 mol) and 50 g of acetic acid (0.83 mol) were mixed at room temperature. Add 12.5 g of ammonia-containing molecular mass concentration of 25% ammonia water and 100 ml of water. heating to 90 C, the reaction is exothermic, maintaining the reaction temperature of 100 C, refluxing reaction for 1 hour (to 1-methyl-1H-pyrazole-4-carbaldehyde reaction is complete), The reaction solution was cooled to room temperature, poured into ice water and quenched and diluted. neutralize until the reaction solution is neutral, extract with ethyl acetate, and dry. After concentrating the product, it is distilled under reduced pressure and recrystallized.The product obtained was 10.2 g, the yield was 95%, and the purity was over 99%.

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

Reference:
Patent; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; (14 pag.)CN108707113; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics