Tag: M.W:100-200

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. 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H14N4O

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.

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:
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;,
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Related Products of 637336-53-9, 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. 637336-53-9, name is Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 6-chloro-N-cyclopropyl-8-((4-methoxybenzyl)(methyl) amino)imidazo [1 ,2-bjpyridazine-3 -carboxamide (id) (125 mg, 0.324 mmol), methyl 4- amino-1-methyl-1H-pyrazole-3-carboxylate (101 mg, 0.648 mmol) [Free based (sodium bicarbonate solutionlEtOAc) from HC1 salt purchased from Art-Chem-BBj, Pd2(dba)3 (29.7 mg, 0.032 mmol), XANTPHOS (37.5 mg, 0.065 mmol) and C52CO3 (422 mg, 1.296mmol) in DMA (2 mL) was degassed by bubbling N2 through the mixture for 5 minutes. The reaction vessel was sealed and heated to 125 C for 8 hr. After cooling to rt, the reaction mixture was partitioned between EtOAc (30 ml) and water (20 ml). The organic layer was extracted with iN NaOH (10 ml) and the combined aqueous layers were washed with EtOAc (20 ml). The aqueous layer was acidified to pH 1 with iN HC1 andthe mixture was transfered to a separatory funnel and the aqueous layer was extracted with EtOAc (3 x 25 ml). The combined organic layers were washed with 10%LiC1 solution (2 x 50 ml) and brine (50 ml). After drying (Na2SO4) and filtration the organic layer was concentrated to afford 4-((3 -(cyclopropylcarbamoyl)-8-((4-methoxybenzyl)- (methyl)amino)imidazo [1 ,2-bj pyridazin-6-yl)amino)- 1-methyl- 1H-pyrazole-3 -carboxylicacid (le) (126 mg, 0.257 mmol, 79 % yield) as a tan solid. LC retention time 2.60 mm [Cj. MS (E+) m/z: 491 (MF-T)

The chemical industry reduces the impact on the environment during synthesis Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SPERGEL, Steven, H.; MERTZMAN, Michael, E.; (132 pag.)WO2018/67432; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 143426-52-2, 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 143426-52-2 as follows.

To a stirred solution of intermediate 1 (0.15 g, 0.73 mmol) in MeCN (10 mL), were added Intermediate 11 (0.14 g , 0.75 mmol) and trimethylamine (0.27 mL, 1.86 mmol ) at RT and the resulting mixture was stirred overnight at RT. After completion of reaction, the reaction mixture was quenched with water (10 mL) and extracted with EtOAc (3 x 30 ml_). The combined organic layer was washed with brine (30 mL), dried over Na2S04, filtered and concentrated under vacuum. The resulting crude material was purified by prep-HPLC (Method B) to get desired compound. Yield: 39% (90 mg, White solid). 1H NMR (400 MHz, DMSO-d6): d 8.45 (d, J = 2.0 Hz, 1 H), 7.77-7.73 (m, 3H), 7.35 (d, J = 8.4 Hz, 2H), 6.93-6.82 (m, 3H), 6.53 (s, 1 H), 4.22 (s, 4H), 3.72 (d, J = 13.2 Hz, 1 H), 3.33-3.27 (m, 1 H), 3.09-3.06 (m, 1 H), 2.97 (t, J = 7.6 Hz, 1 H), 2.19-2.06 (m, 2H), 1.81-1.71 (m, 2H), 1.70-1.56 (m, 1 H). LCMS: (Method A) 362.1 (M+H), Rt. 97.70 min, 88.96% (Max). HPLC: (Method A) Rt. 2.88 min, 97.88% (Max).

According to the analysis of related databases, 143426-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; WISHART, Grant; KULKARNI, Santosh S.; RAKESH, Paul; (338 pag.)WO2020/39027; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

10199-68-5, name is 4-Phenyl-1H-pyrazole, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 4-Phenyl-1H-pyrazole

To a solution of l,2-dibromoethane (130 mg, 0.694 mmol) and 4-phenyl-lH- pyrazole (100 mg, 0.694 mmol) in DMF (2 mL) was added CS2CO3 (226 mg, 0.694 mmol) portion-wise. The mixture was stirred at RT for 30 min and at 65 C for 1.5 hrs. LCMS showed the starting material was consumed completely and product was detected. The mixture was poured into water (10 mL) and extracted with ethyl acetate (10 mL*3). The combined organic layers were washed with brine (10 mL), dried over NaiSOr. filtered and concentrated to residue. The residue was purified by prep-TLC (pet. etherethyl acetate; 2: 1) to give the desired product l-(2-bromoethyl)-4-phenyl-lH-pyrazole (60 mg, 0.239 mmol, (0989) 34.4 % yield) as yellow oil. LCMS (M +H) = 251.0; Retention time (10 mM NH4HC03) = 1.40 min.

The synthetic route of 10199-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; GILLIS, Eric P.; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M.; (367 pag.)WO2019/244066; (2019); 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 5775-82-6 as follows. name: 4-Bromo-1,3-dimethyl-1H-pyrazole

To a suspension of 4-bromo-l,3-dimethyl-pyrazole (5.00 g, 28.60 mmol) in anhydrous 1,4-dioxane (100.0 mL) were added 4,4,4′,4′,5,5,5′,5l-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (8.71 g, 34.32 mmol), acetoxy potassium (5.63 g, 57.41 mmol) and Pd(dppf)2Cl2 dichloromethane complex (2.38 g, 2.86 mmol). The mixture was degassed and refilled with nitrogen for several times and then heated to 100 C and stirred overnight. The mixture was concentrated in vacuo. The residue was diluted with water (30 mL), and the resulting mixture was extracted with EtOAc (50 mLchi3). The combined organic layers was dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica chromatography (EtOAc/PE (v/v) = 1/20 to 1/8) to afford the title compound as brown sticky liquid (3.80 g, yield 60%).MS (ESI, pos. ion) m/z: 223.3 [M+H]+

According to the analysis of related databases, 5775-82-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Xiaobo; LI, Mingxiong; ZHANG, Tao; HU, Haiyang; WU, Yanjun; (139 pag.)WO2018/169700; (2018); 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. 7119-95-1, name is 1-Nitropyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 7119-95-1

3-Nitro-lH-pyrazolew; [539] [Ref.: Janssen, J.W.A.M. and Habraken, C.L., J. Org. Chem., 1971,36,3081.] A solution of l-nitro-ll/’-pyrazole (3.0g, 0.026 mol) in anisole (200mL) was heated at 145C overnight. The mixture was cooled to rt, the white solid was collected by filtration and washed with hexanes. The mother liquid was diluted with hexanes (500mL) and cooled to -20C, and the resulting off-white solid was collected and combined with the previous solid.LC-MS (ES, Pos.): 1 14 [MH+]. ‘H NMR (DMSO-d6, 400 MHz): 5 = 7.04 (d, J= 2.5 Hz, 1H),8.04 (d, /= 2.5 Hz, 1H), 13.96 (br s, 1H).

The synthetic route of 7119-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5203-77-0, 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. 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol, This compound has unique chemical properties. The synthetic route is as follows.

At room temperature, 1,3-dimethyl-1hydro-pyrazole-5-ol (0.65 g, 0.0058 mol) and (0.48 g, 0.012 mol) sodium hydroxide were sequentially dissolved in 20 ml of dichloromethane.The low temperature bath was cooled to -4 C. To the above mixture was added dropwise 3,7-dichloro-5-(methylsulfonyl)-6-(((tetrahydrofuran-3-yl)methoxy)methyl)quinoline-8-carbonyl chloride (3.81 g, 0.0084 mol),The dropping rate was 4 drops / 30 seconds. After the addition was complete, the mixture naturally rose to room temperature and reacted for 5 hours.To the reaction mixture was added 10 ml of a saturated aqueous sodium hydrogen carbonate solution, and dichloromethane (3 * 15 ml) was extracted. The organic layers were combined, washed with water (1 * 15 ml), washed with saturated brine, and dried over anhydrous magnesium sulfate.The product was dissolved under reduced pressure to obtain 2.12 g of the product with a yield of 70%

The chemical industry reduces the impact on the environment during synthesis 1,3-Dimethyl-1H-pyrazol-5-ol. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shandong Joint Pesticide Co., Ltd.; Tang Jianfeng; Chi Huiwei; Wu Jianting; Yuan Xue; Liu Ying; (52 pag.)CN110615781; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 4522-35-4, A common heterocyclic compound, 4522-35-4, name is 3-Iodo-1H-pyrazole, molecular formula is C3H3IN2, 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.

INTERMEDIATE 30 4- (3-Iodo-lH-pyrazol-l-yl)-2-methoxy-5-(trifluoromethyl)pyridine To a solution of 3-iodopyrazole (0.30 g, 1.547 mmol), in DMSO (7.73 mL) was added sodium hydride (60% in oil, 0.068 g, 1.701 mmol) and stirred for 0.5 h before 4-iodo- 5- trifluoromethyl-2-methoxypyridine (0.469 g, 1.547 mmol) was added. The reaction mixture was stirred at 80 C for 4 h. The reaction was quenched by the addition of water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 24 g, 0-20 % EtOAc in hexanes) to give 4-(3-iodo-lH-pyrazol-l-yl)-2-methoxy-5-(trifluoromethyl)pyridine, as a white solid. LCMS calc. = 369.96; found = 369.83 (M+H)+. NMR (500 MHz, CDC13): delta 8.58 (s, 1 H); 7.63 (s, 1 H); 7.01 (d, J ^ 2.8 Hz, 1 H); 6.65 (d, J= 2.6 Hz, 1 H); 4.03(d, J= 3.3 Hz, 3 H).

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.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 82560-12-1, 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. 82560-12-1, name is 3-Amino-5-tert-butylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3-tert-butyl-1H-pyrazol-5-amine 7 (0.139 g, 1 mmol), methyl ester 6 (0.199 g, 1 mmol) and DMSO (2 mL) was stirred at ambient temperature during 2 h. After complete disappearance of the starting materials (monitored by TLC), the solid formed was collected by filtration and washed with MeOH/H2O (1/2) (3 × 2 mL), to afford compound 8. Orange solid, 76% yield; m.p: 241-242 C. FTIR nu (cm-1): 3371 (NH), 3316 (NH), 3117, 2955, 1705 (CO), 1625 (CN), 1532 and 1323 (NO2), 1122 (C-O); 1H NMR (CDCl3) delta 1.39 (s, 9H, tBu), 3.95 (s, 3H, OCH3), 5.98 (s, 1H, Pz-CH), 8.06 (d, 1H, J = 9.1 Hz), 8.13 (dd, 1H, J = 9.1 Hz, J = 1.8 Hz), 8.94 (d, 1H, J = 1.8 Hz), 10.07 (bs, 1H, Pz-NH) ppm, the aniline NH is missing; 13C NMR (CDCl3) delta 30.0 (tBu), 31.2 (Cq, tBu), 52.2 (OCH3), 94.9 (Pz-CH), 117.2, 119.5 (Cq), 128.9, 132.1 (Cq), 136.2, 144.3 (Cq), 148.0 (Cq), 154.6 (Cq), 165.5 (CO) ppm. MS (EI) m/z (%): 318 (100, M+), 287 (15, M – CH3). Anal. Calcd. for C15H18N4O4: C, 56.60; H, 5.70; N, 17.60. Found: C, 56.54; H, 5.83; N, 17.46.

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-Amino-5-tert-butylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Abonia, Rodrigo; Cortes, Edwar; Insuasty, Braulio; Quiroga, Jairo; Nogueras, Manuel; Cobo, Justo; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4062 – 4070;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 42027-81-6,Some common heterocyclic compound, 42027-81-6, name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, molecular formula is C5H7N3O3, 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: 2a (0.32 g, 0.002 mol) was dissolved in 20 ml ethanol in a roundbottomedflask and Pd/C (10%, 0.1 g) was added which reacted at 60 Cfor 12 h under hydrogen atmosphere. The Pd/C was recycled by filtrationand the ethanol was recycled by evaporation to give the amineas purple oil which was retained in the round-bottomed flask. Theamine was used for next reaction without purification, because it waseasily oxidized. Then, added 6-bromo-4-chloroquinazoline (0.36 g,0.0015 mol) and isopropanol (30 ml) to the round-bottomed flask aboveand stirred at 90 C for 4 h. The isopropanol was removed under reducedpressure and the residue was purified through a column chromatographyon silica with chloroform/methanol (V:V 10:1) as a whitesolid (0.43 g, 86.0% yield).

The synthetic route of 42027-81-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ding, Huai-Wei; Wang, Shu; Qin, Xiao-Chun; Wang, Jian; Song, Hong-Rui; Zhao, Qing-Chun; Song, Shao-Jiang; Bioorganic and Medicinal Chemistry; vol. 27; 13; (2019); p. 2729 – 2740;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics