Tag: M.W:100-200

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Synthesis called An epoxide ring-opening reaction via hypervalent silicate intermediate: Synthesis of statine, Author is Konno, Hiroyuki; Toshiro, Emi; Hinoda, Naoyuki, which mentions a compound: 17190-29-3, SMILESS is N#CCC(O)C1=CC=CC=C1, Molecular C9H9NO, SDS of cas: 17190-29-3.

The azide- and cyanide-opening reaction of epoxide with TBAF and TMSN3 in THF or TBAF and TMSCN in MeCN occurred regioselectively to afford β-hydroxy azides and cyanides in good yield. These hypervalent silicates are highly effective as nucleophilic azide and cyanide donors under mild conditions. This methodol. was applied to the preparation of statine.

Here is a brief introduction to this compound(17190-29-3)SDS of cas: 17190-29-3, if you want to know about other compounds related to this compound(17190-29-3), you can read my other articles.

Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Condensation of benzaldehyde with bromoacetonitrile》. Authors are Vul’fson, N. S.; Vinograd, L. Kh..The article about the compound:3-Hydroxy-3-phenylpropanenitrilecas:17190-29-3,SMILESS:N#CCC(O)C1=CC=CC=C1).Computed Properties of C9H9NO. Through the article, more information about this compound (cas:17190-29-3) is conveyed.

To a refluxing solution of 21.3 g. BzH, 32 ml. C6H6, and 8 ml. Et2O containing 18 g. activated Zn dust there was added in 0.5 hr. 24 g. BrCH2CN. After refluxing 2 hrs. the cooled mixture was stirred 1 hr. with 120 ml. 10% H2SO4, filtered, separated, the organic layer extracted with 10% H2SO4 and H2O, and the combined aqueous layers extracted with C6H6 and combined with the original organic layer. Distillation gave 14.2 g. PhCH(OH)CH2CN, b4-5 147-51°. This shaken with 12% H2O2 in the presence of 1 drop of NaOH and little EtOH gave the corresponding amide, m. 120° (from EtOH). Refluxing the nitrile with 4N NaOH gave 63.6% PhCH:CHCO2H.

Here is a brief introduction to this compound(17190-29-3)Computed Properties of C9H9NO, if you want to know about other compounds related to this compound(17190-29-3), you can read my other articles.

Reference:
Pyrazole – Wikipedia,
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Synthetic Route of 16617-46-2, 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. 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of aldehyde (2 mmol), 3-aminopyrazole (1 mmol), and p-toluenesulfonic acid catalyst (20 mol percent) in MeCN (5 mL) was magnetically stirred for 24 h in room temperature. Next TsCH2NC (1 mmol) was added and the reaction mixture was stirred for 24 h in room temperature. After completion of the reaction, which was followed by TLC EtOAc/petroleum ether 4:1, the reaction mixture was filtered, and the precipitate washed with methanol. Finally pure solid product was obtained by column chromatography.

The synthetic route of 3-Amino-1H-pyrazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rahmati, Abbas; Eskandari-Vashareh, Miranda; Alizadeh-Kouzehrash, Meysam; Tetrahedron; vol. 69; 21; (2013); p. 4199 – 4204;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31037-02-2,Some common heterocyclic compound, 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H11N3O2, 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.

The acid chloride reaction solution was synthesized in the same manner as in Example 1.75 g of water, 67 g of pyrazole amine, 42 g of sodium carbonate and 5 g of triethylamine were added to 1000 ml, cooled to 0 to 5 C, and acyl chlorideThe reaction solution was controlled at a temperature of 5 to 10 C. The dropwise addition was completed and the reaction was completed for 1 hour. The reaction was completed, the layers were separated and the organic phase was dissolved to obtain a crude product.Add 200g of methanol heated to 50 C dissolved, cooled to 5 C, precipitated the solid, filtered to give the product as a white solid, yield:82%, content: 95%.

The synthetic route of 31037-02-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Fuding Chemical Co., Ltd.; Liu, Dongwei; Cheng, Lizhong; Chang, Qing; Dong, Hailong; Zhu, Ruiyu; Gu, Junkun; (11 pag.)CN106631896; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 5334-43-0, 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. 5334-43-0, name is 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 5-amino-1-phenyl-1H-pyrazole-4-carbonitriles (7-12)(0.01 mol) and 20 mL of formic acid was stirred and allowed to reflux for 12 h. The reaction mixture was poured into 50 mL of ice-cold water. The precipitate was collected by filtration and washed with water to produce 13-18 in 68-89% yield. 1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (13). Yield: 74%.MP:>300 C. IR (cm-1): 3116; 1727; 1660; 1591. 1H NMR (400 MHz,DMSO-d6, TMS, delta in ppm): 8.06-7.39 (m; 5H; HAr); 8.20 (d; 1H;J=3.8 Hz; H6); 8.34 (s; 1H; H3); 12.46 (s; 1H; NH). 13C NMR(100 MHz, DMSO-d6, TMS, delta in ppm): 107.6 (C3a); 121.7 (C2?, C6?);127.1 (C4?); 129.1 (C3?, C5?); 135.9 (C3); 138.2 (C1?); 148.7 (C6); 151.8(C7a); 157.2 (C4). EI [M+1]+ 213.07.

The synthetic route of 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feitosa, Livia M.; da Silva, Edson R.; Hoelz, Lucas V.B.; Souza, Danielle L.; Come, Julio A.A.S.S.; Cardoso-Santos, Camila; Batista, Marcos M.; Soeiro, Maria de Nazare C.; Boechat; Pinheiro, Luiz C.S.; Bioorganic and Medicinal Chemistry; vol. 27; 14; (2019); p. 3061 – 3069;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 175137-46-9, A common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, 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 2,3,6-trichloro-5-nitropyridine (1.62 g, 7.10 mmol) and DIEA (1.24 ml, 7.1 mmol) in THF (25 ml) was added dropwise a solution of 5-cyclopropyl-lH-pyrazol-3- amine (0.70 g, 5.68 mmol) in THF (5 ml) at 0 C. After addition, the reaction mixture was stirred at 25 C for 24 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 1.5 : 1) to give the title compound as a yellow solid (0.83 g, 47%). NMR (400 MHz) 12.39 (s, IH), 10.12 (s, IH), 8.77 (d, J= 1.2 Hz, IH), 6.35 (s, IH), 1.95 (m, IH), 0.96 (m, 2H), 0.71 (m, 2H). MS: Calcd.: 313; Found: [M+H]+ 314

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82392; (2006); 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 78703-53-4 as follows. Application In Synthesis of 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

General procedure: 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid of formula (III) (7.76 g, 40 mmol)Reflowed with thionyl chloride (47.6 g, 0.4 mol) for 4 hours.When the reaction system turns into a pale yellow transparent liquid,Continue to react for 30 minutes,The reaction stops,After cooling to room temperature, it was distilled under reduced pressure.1,3-dimethyl-1H-pyrazole-4-yl chloride,1,3-Dimethyl-1H-pyrazole-4-yl chloride (2mmol)Add 15ml of dichloromethane,Join(R)-1-phenethyl-1-amine(2.1mmol),Then triethylamine (0.3 g, 3 mmol) was slowly added dropwise at room temperature overnight;TLC (EA: PE=2:1(V)) tracking,After the reaction was completed, it was extracted three times with a dichloromethane/water = 1:1 (V) system.Concentrated organic layer,Extracted with toluene or 75% ethanol,Column chromatography (EA: PE = 2:1 (V)),Obtained (K19)(R)-1,3-dimethyl-N-(1-phenethyl)-1H-pyrazole-4-carboxamide;

According to the analysis of related databases, 78703-53-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang University of Technology; Jin Tao; Wang Han; Tan Chengxia; Weng Jianquan; Han Liang; Liu Xinghai; (9 pag.)CN109156471; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 143426-52-2, 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. 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of methyl 2-amino-3,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.69 g), 1-(4-(chloromethyl)phenyl)-1H-pyrazole (0.46 g), 2 M aqueous sodium carbonate solution (2.26 mL) and DME (20 mL) was added (1,1-bis(diphenylphosphino)ferrocene)dichloropalladium(II) dichloromethane adduct (0.09 g) under an argon atmosphere and the mixture was stirred at 80 C. overnight. The reaction mixture was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.65 g). MS: [M+H]+ 336.1

The synthetic route of 1-(4-(Chloromethyl)phenyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Sugimoto, Takahiro; Suzuki, Shinkichi; Sakamoto, Hiroki; Yamada, Masami; Nakamura, Minoru; Kamata, Makoto; Shimokawa, Kenichiro; Ogino, Masaki; Kimura, Eiji; Murakami, Masataka; Kojima, Takuto; Yonemori, Jinichi; (63 pag.)US10548899; (2020); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 34334-96-8,Some common heterocyclic compound, 34334-96-8, name is 3-Methyl-5-nitro-1H-pyrazole, molecular formula is C4H5N3O2, 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.

Add acetonitrile (56 mL) to a mixture of 5-methyi-3-nitro-1H-pyrazoie (3.0 g, 22 mniol), potassium carbonate (6.2 g, 2.0 eq), and I -bromo-3-methoxypropane (3.8 g, 1.1 eq). Stir at 65 C overnight. Cool to EtOAc (50 mE) and filter. Concentrate the filtrate in vacuo. Subject the residue to normal phase chromatography, eluting with 35% EtOAc in hexanes, to give the title compound (3.3 g, 70%). MS (ES) ,n/z 200 (M-fH).

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

Reference:
Patent; ELI LILLY AND COMPANY; BASTIAN, Jolie Anne; CLAYTON, Joshua Ryan; COATES, David Andrew; SALL, Daniel Jon; WOODS, Timothy Andrew; (58 pag.)WO2018/13486; (2018); 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 solution of 3-methyl-4-nitro-lH-pyrazole (1 -1, 398 nig, 3.13 mmol) in DMF (10 niL) was added NaH (125 mg, 3.13 mmol, 60% purity) at 0 C, then the reaction was stirred at 20 C for 1 h. Then, (3-methyl- 5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyridin-6-yl) methanesulfonate (604 mg, 2.61 mmol, 70% purity) in DMF (4 mL) was added to the solution at 20 C. Then, the mixture was stirred at 80 C for 12 h. The reaction solution was added with NH4Q solution (20 ml,), extracted with DCM:MeOH (20 mL chi 3, ratio=3: l). The organic layers were combined, dried over Na2S04, filtered and concentrated under reduced pressure. The crude product was purified by prep-TLC (DCM:MeOH = 5: 1) to give a mixture of 3-niethy3~6~(3-methyi-4~nitro^ and 3- methyl-6-(5~methyl-4-nitro-pyra^ as a yellow gum. LCMS: RT 0.925 min, m/z = 263.1 | M – H j ‘ . NMR (400 MHz, CDC13): delta 8.25 (s, 0.6 H), 8.13 (s, 0.3 H), 4.68 – 4.81 (m, 1 H), 4.14 – 4.42 (m, 2 H), 3.02 – 3.31 (m, 2 H), 2.77 (s, 1 H), 2.55 (s, 2 H), 2.44 – 2.53 (m, 4 H), 2.43 (s, 1 1H 1).

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; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics