Tag: M.W:100-200

Related Products of 881668-70-8, 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 881668-70-8 as follows.

4,5-Dichloropyrazole-3-carboxyh’c acid (TV”)Chlorine gas was bubbled slowly through a stirred solution of 5-chloropyrazole-3- carboxylic acid (Intermediate II, 3.00 g, 20.5 mmol) in water (2.0 L) at rt over 3 h. The solution was stirred for 18 h in an open flask and then concentrated in vacuo. The slurry was extracted with ethyl acetate (3×100 mL), the combined extracts were washed with NaCl (sat., aq.; 100 mL) and dried (Na2SO4). The solvent was removed in vacuo to give the product as a white powder. Yield 3.20 g (86 %). MS (MT-H) Wk= 179. 1H NMR (DMSO^6, 400 MHz) delta 14.44 (s, IH), 14.09 (s, IH). 13CNMR (CD3OD, 100 MHz) delta 160.0; 139.6; 133.1; 112.4.

According to the analysis of related databases, 881668-70-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOLIPOX AB; WO2007/51981; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1260243-04-6, 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. 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3-amino-4-carbethoxy pyrazole (1, 4 g, 1 mmol, 1 equiv) in acetonitrile (60 mL) and sodium hyride (1.5 g, 2 equiv) was stirred in a 250 mL round bottom flask for 1 h under ice cold conditions. Benzylchloride (6 mmol, 1.5 equiv) was added to the reaction mixture and further stirred at room temperature for 12 h. The mixture was extracted with ethyl acetate (3 * 10 mL). The organics were washed, dried on anhydrous Na2SO4, evaporated on a rotary evaporator to afford the crude product. The crude product was recrystallized (MeOH) to get pure compound 6a. Yield: 60%, white solid; mp: 161-162 C; IR (KBr): 3465, 3301, 1693, 1605 cm-1; 1H NMR (400 MHz, DMSO-d6): delta = 1.24 (t, 3H, J = 6.96 Hz, CH3), 4.17 (q, 2H, J = 6.92 Hz, OCH2), 5.35 (s, 2H, CH2), 7.35-7.24 (m, 5H), 8.08 (s, 1H, CH); 13C NMR (100 MHz, DMSO-d6): delta = 55.09, 59.52, 98.09, 127.61, 127.78, 128.17, 128.25, 128.72, 128.93, 133.63, 137.28, 157.07, 164.14.

The chemical industry reduces the impact on the environment during synthesis Ethyl 5-amino-1H-pyrazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Baviskar, Ashish T.; Banerjee, Uttam C.; Gupta, Mukesh; Singh, Rajveer; Kumar, Sunil; Gupta, Manish K.; Kumar, Sanjeev; Raut, Satish K.; Khullar, Madhu; Singh, Sandeep; Kumar, Raj; Bioorganic and Medicinal Chemistry; vol. 21; 18; (2013); p. 5782 – 5793;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 28466-21-9, name is 1,3,5-Trimethyl-1H-pyrazol-4-amine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H11N3

Reference Example 37 Ethyl 4-{4-chloro-7-(1-ethylpropyl)-2-[(1,3,5-trimethyl-1H-pyrazol-4-yl)amino]-1H-benzimidazol-1-yl}butanoate A mixture of ethyl 4-[2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (Reference Example 33; 371 mg, 1.00 mmol), 4-amino-1,3,5-trimethylpyrazole (375 mg, 3.00 mmol) and p-toluenesulfonic acid monohydrate (190 mg, 1.00 mmol) in 1-methyl-2-pyrrolidinone (3 mL) was stirred at 150 C. for 16 hr. After cooling, aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. Organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluding with a 0-5% methanol/ethyl acetate gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/n-hexane to give the title compound (340 mg, 0.74 mmol, 74%) as a colorless solid. mp 177-178 C. 1H NMR (CDCl3) delta 0.86 (t, J=7.3 Hz, 6H), 1.28 (t, J=7.0 Hz, 3H), 1.64-1.85 (m, 4H), 2.03-2.16 (m, 2H), 2.20 (s, 3H), 2.22 (s, 3H), 2.44-2.51 (m, 2H), 2.87-2.99 (m, 1H), 3.74 (s, 3H), 4.10-4.24 (m, 4H), 6.79 (d, J=8.3 Hz, 1H), 6.90 (s, 1H), 7.08 (d, J=8.3 Hz, 1H). MS Calcd.: 459; Found: 460 (M+H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 28466-21-9.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/186879; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 5932-27-4, name is Ethyl 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. Quality Control of Ethyl 1H-pyrazole-3-carboxylate

Methyl 1H-pyrazole-3-carboxylate (0.500 g, 3.96 mmol) was dissolved in dry MeCN (12 mL), then 2,2-dimethyloxirane (0.53 1 mL, 5.95 mmol) was added, followedby cesium carbonate (1.94 g, 5.95 mmol). The reaction mixture was stirred at 150 ¡ãC under microwave irradiation for 30 mm. The reaction mixture was cooled to rt, diluted with EtOAc (transesterification occurred upon EtOAc addition). The residue was purified by flash chromatography (solid loading on CELITE?, 20-100percent EtOAc/Hex) affording Intermediate 17A (0.305 g, 36percent yield) as a colorless syrup. MS(ESI) m/z: 213.0 (M+H)?H NMR: (400 MHz, DMSO-d6) oe ppm 7.50 (d, J=2.4 Hz, 1H), 6.83 (d, J2.4 Hz, 1H),4.40 (q, J=7.0 Hz, 2H), 4.17 (s, 2H), 2.77 (s, 1H), 1.39 (t, J=7.2 Hz, 3H), 1.20 (s, 6H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 100114-57-6,Some common heterocyclic compound, 100114-57-6, name is 3-Cyclopropyl-1H-pyrazole, molecular formula is C6H8N2, 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.

[00759] Intermediate 81a: benzyl 2-(3-cyclopropylpyrazol-1-yI)acetate[00760] A suspension of 3-cyclopropyl-1 H-pyrazole (100mg, 0.g2mmol) and potassium carbonate (383mg, 2.77mmol) in MeCN (3mL) was left to stir at room temperature for 30 minutes before the addition of benzyl bromoacetate (0.21 mL, 1 .3gmmol) and sodium iodide (139mg, 0.g2mmol). The resulting mixture was heated to 60 C and left to stir overnight. The reaction was quenched by theaddition of water (2OmL) and extracted with EtOAc (3 x 2OmL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography using an eluent of 0-20% EtOAc in heptane to give benzyl 2-(3-cyclopropylpyrazol- 1-yl)acetate (204mg, 0.8Ommol, 86% yield) as a colourless oil.1H NMR (CDCI3,400MHZ) O/ppm: 7.42-7.32 (6H, m), 5.98 (1H, d, J= 2.3Hz), 5.21 (2H, 5), 4.89 (2H,5), 1.64 (1H, tt, J= 8.3Hz, 5.0Hz), 0.97-0.88 (2H, m), 0.77-0.72 (2H, m). MS Method 2: RT: 1.88 mi mlz 257.0 [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 3-Cyclopropyl-1H-pyrazole, its application will become more common.

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 13808-62-3,Some common heterocyclic compound, 13808-62-3, name is 4-Methyl-3-phenyl-1H-pyrazole, molecular formula is C10H10N2, 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 (E)-2-methyl-3-phenylacrylaldehyde (1c) (146 mg, 1.0 mmol) and TsNHNH2 (205 mg, 1.1 mmol) in CH3CN (2 mL) were stirred at room temperature for 3 h and then CH3CN (2 mL), NaOH (44 mg, 1.1 mmol) were added and the mixture was heated at reflux for 15 h, then NaOH (60 mg, 1.5 mmol) and benzyl bromide (255 mg, 1.5 mmol) were subsequently added and the mixture was stirred at room temperature for 2 h. The product was extracted with Et2O and the organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel afforded the desired product 4k as colorless oil (233 mg, 94%).

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

Reference:
Article; Tang, Meng; Zhang, Fu-Min; Tetrahedron; vol. 69; 5; (2013); p. 1427 – 1433;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 402-61-9, 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. 402-61-9 name is 5-Methyl-1H-pyrazole-3-carboxylic acid, 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.

Example 1 lambda/-[6-(1H-lndol-4-yl)-1H-indazol-4-yl]-5-methyl-1H-pyrazole-3-carboxamide 5-Methyl-1 H-pyrazole-3-carboxylic acid (10mg) in DMF (0.2ml) was treated with N- [(dimethylamino)(3H-[1 ,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-/V- methylmethanaminium hexafluorophosphate (27mg) in DMF (0.2ml) and DIPEA (0.03ml). The reaction mixture was shaken for five min prior to treatment with 6-(1H-indol-4-yl)-2- (tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (20mg) in DMF (0.2ml). The reaction mixture was shaken for five min and left to stand at 220C for 18h. The solvent was removed in vacuo and the product re-dissolved in methanol (1 ml) prior to application on to an SCX SPE cartridge (1g). The product was eluted after 1 h with 2M ammonia in methanol (2x3ml), the fractions were combined and concentrated under a stream of nitrogen using blow down apparatus. Purification by mass directed preparative HPLC (Method C) afforded the title compound. LC/MS R1 2.91 min m/z 357 [MH+]. Method A

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147188; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 4522-35-4, 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. 4522-35-4, name is 3-Iodo-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 2: 3-iodo-l-methyl-lH-rhoyrazole.To a stirred solution of 3-iodo-leta-rhoyrazole (0.5 g, 2.6 mMol) in anhydrous DMF (5.0 mL) was added iodor¡ãethane (3.7 g, 25.8 mMol). The resulting solution was cooled to 00C, and NaH (0.11 g, 2.8 EPO mMol, 60% dispersion in mineral oil) was added. The reaction mixture was allowed to warm to ambient temperature, and was stirred for 15 minutes. Water (20 mL) was added, and the resulting solution was extracted with EtOAc (1 x 30 mL). The organic layer was washed with water (2 x 30 mL), and brine (1 x 30 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated to afford the title compound. LRMS (ESI) calculated for C4H5IN2 [M+H]+, 208.9; found 209.0.

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

Reference:
Patent; MERCK & CO., INC.; WO2007/35309; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6825-71-4, name is Ethyl 3,5-diamino-1H-pyrazole-4-carboxylate, molecular formula is C6H10N4O2, 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. Application In Synthesis of Ethyl 3,5-diamino-1H-pyrazole-4-carboxylate

Another exemplary study was carried out as follow: Compound J and AcOH (7.5 volumes) were charged to an appropriately sized jacketed reactor. Mixing was started and the jacket was set to maintain an internal temperature of 25 C . Tetramethoxypropane (1.01 equivalents) was charged to the reactor and the j acket was set to maintain an internal temperature of 95 C. Once at temperature, the reaction continued mixing for 1.5 hours and then an IPC sample was taken. The passing criteria for this IPC was 60 C to prevent premature precipitation. Once the target volume was reached the jacket was set to maintain an internal temperature of 50 C. A 4 M solution of NaOH was then charged to the reactor via cannula to neutralize the remaining AcOH. This typically required approximately 10 volumes of the base solution. The neutralization was monitored by pH probe. Solids began to precipitate during the course of the charge. Once neutralized, the slurry was cooled to 20 C and held at that temperature for 1 hour prior to isolation via Buchner funnel. The cake was washed twice with 2 volumes of water and once with 2 volumes of MeOH. The solids were then dried to constant weight in a vacuum oven to provide Compound H. This procedure had been performed on 110 g scale to produce a granular light brown solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6825-71-4, its application will become more common.

Reference:
Patent; INFINITY PHARMACEUTICALS, INC.; CRENIER, Louis; LESCARBEAU, Andre; SHARMA, Praveen; GENOV, Daniel G.; (324 pag.)WO2017/48702; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

General procedure: A mixture of substituted 3-(2-aryl-2-oxoethylidene)indolin-2-one 1 (1 mmol), 1,3-dimethylurea (2, 1.2 mmol) or 5-amino-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (4, 1 mmol), PTSA¡¤H2O (0.3 mmol), and MeCN (5 mL) was added to a 25 mL flask and reacted at 80 C (monitored by TLC) about 2 h. After completion, the mixture was cooled to r.t. and the precipitate obtained was isolated by filtration and drying. Compounds 3 or 5 were purified by recrystallization (DMF or EtOH).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4149-06-8.

Reference:
Article; Dai, Lei; Shu, Ping; Wang, Zhansheng; Li, Qingyang; Yu, Qiuyu; Shi, Yanhui; Rong, Liangce; Synthesis; vol. 49; 3; (2017); p. 637 – 646;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics