Tag: M.W:200-300

Application of 423165-07-5,Some common heterocyclic compound, 423165-07-5, name is exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, molecular formula is C13H22N4, 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 7: 1-acetyl-N-(3-chloro-4-methylphenyl)-N-(3-(3-exo-(3-isopropyl-5-methyl-4-hydro-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl)propyl)-4-piperidinylcarboxamide (compound 11) A solution of 1-acetyl-N-(3-chloro-4-methylphenyl)-N-(3-chloropropyl)-4-piperidinylcarboxamide (185 mg, 0.5 mmol), the product prepared in step 6 (129 mg, 0.55 mmol) and triethylamine (0.21 mL, 1.5 mmol) in acetonitrile (5 mL) was stirred and refluxed for 24 hours, and then vaporized off the solvent, diluted with ethyl acetate, and washed with water and saline respectively. The separated organic phase was dried with sodium sulfate and concentrated under reduced pressure. The concentrate was separated through column chromatography (dichloromethane/methanol=20/1 to 10/1, v/v) to give a yellowish foam-like product (28 mg, yield: 10%). 1HNMR (CDCl3, 300 MHz) delta: 7.36-7.30 (m, 1H), 7.20 (s, 1H), 7.01-6.97 (m, 1H), 4.55-4.48 (m, 1H), 4.30-4.20 (m, 1H), 3.49-3.44 (m, 1H), 3.31 (br-s, 2H), 3.00-2.96 (m, 1H), 2.89-2.79 (m, 1H), 2.43 (s, 3H), 2.48-2.35 (m, 6H), 2.05 (s, 3H), 2.18-1.96 (m, 5H), 1.75-1.62 (m, 12H), 1.38-1.25 (m, 6H);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, its application will become more common.

Reference:
Patent; SHANGHAI TARGETDRUG CO., LTD.; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; US2011/251192; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 423165-07-5, These common heterocyclic compound, 423165-07-5, name is exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane, 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.

General procedure: To an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C.

Statistics shows that exo-3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane is playing an increasingly important role. we look forward to future research findings about 423165-07-5.

Reference:
Article; Viveka, T. Lakshmi; Sharada, L. Nalanda; Asian Journal of Chemistry; vol. 30; 9; (2018); p. 2029 – 2034;,
1,2,3-Triazole – Wikipedia,
Triazoles – 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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C2HBr2N3

General procedure: 3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) or 3-chloro-1,2,4-triazole (300 mg, 2.9 mmol), o-quinone methide precursor 2 (2.9mmol), and K2CO3 (1.2 g, 8.7 mmol) were refluxed for 4 h in DMF (10mL). After completion of the reaction, the mixture was cooled, andpoured into H2O (30 mL). The precipitate formed was collected by filtration,washed with H2O, dried, and recrystallized.

The synthetic route of 7411-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Osipov, Dmitry V.; Osyanin, Vitaly A.; Voskressensky, Leonid G.; Klimochkin, Yuri N.; Synthesis; vol. 49; 10; (2017); p. 2286 – 2296;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid, belongs to Triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: Triazoles

A solution of 1 , 1 -dimethyl-4-(((3i?,6i?)-6-methylpiperidin-3-yl)oxy)furo[3.4- c]pyridin-3(lH)-one hydrogen chloride (0.050 g, 0.16 mmol), 2-fluoro-6-(2H)-l,2,3-triazol-2-yl) benzoic acid (0.036 g, 0.18 mmol), benzotriazole-l-yl-oxy-tris-(dimethylamino)-phosphonium hexaflurophosphate (Bop, 0.092 g, 0.21 mmol), and triethylamine (0.067 mL, 0.48 mmol) in DMF (1 mL) was stirred at RT overnight. The reaction was concentrated in vacuo and azeotroped 3x with toluene. The residue was purified by silica gel gradient chromatography (0-80% ethyl acetate in hexanes), providing the titled compound. HRMS m z (M+H) 466.1890 found, 466.1887 required.

The synthetic route of 1186050-58-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/95442; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 774608-89-8, 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 774608-89-8 as follows.

Ethyl 5-bromo-2H-1 ,2,4-triazole-3-carboxylate (Hechung Huaxue, 2004, 12(2), 191-193, Chem. Abs. 141 :350095) (3.11 g, 14 mmol) was dissolved in methanol (50 ml) and cooled to 0 0C. Trimethylsilyl diazomethane (-14 ml of a 2 M solution in ether) was added until a pale yellow colour persisted and the reaction was warmed to room temperature and quenched by the addition of excess acetic acid. It was then evaporated and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic extract was dried, filtered and evaporated to yield a residue which was purified and separated into its three isomers by silica chromatography using ethyl acetate / petrol. Isomer A (least polar) (1.2 g, 5.1 mmol). 1H NMR (DMSO) delta 4.36 (2 H, q, J = 7 Hz), 4.10 (3 H, s), 1.32 (3 H, t, J=V Hz)Isomer B (medium polarity) (0.47 g, 2.0 mmol). 1H NMR (DMSO) 64.31 (2 H, q, J = 7 Hz), 3.92 (3 H, s), 1.29 (3 H, t, J = 7 Hz) Isomer C (most polar) (0.37 g, 1.6 mmol). 1H NMR (DMSO) 54.38 (2 H, q, J = 7 Hz), 3.82 (3 H, s), 1.33 (3 H, t, J = 7 Hz) Combined yield 62 %.

According to the analysis of related databases, 774608-89-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PARADIGM THERAPEUTICS LTD.; WO2007/582; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 22300-52-3, 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 22300-52-3 as follows.

The 10.0g (44.1mmol) 4,5- dibromo -2H-1,2,3- triazole (commercially available) was dissolved in 90ml of tetrahydrofuran was added 6.1g (44.2mmol) of potassium carbonate, cooled to -10 , was added 7.5g (53mmol) of methyl iodide.In the 35 ~ 40 to react until the reaction is complete.50ml of water was added, the tetrahydrofuran was distilled off, 90ml and extracted with methyl tert-butyl ether, dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure, the residual solid was added methyl tert-butyl ether, 10ml, 70ml of n-hexane was added slowly, solid precipitation, the addition was completed, stirring at room temperature for 1 to 2 hours.Filtered to give pure 4,5-dibromo-1-methyl -1H-1,2,3- triazole 5.8g, 57percent yield.

According to the analysis of related databases, 22300-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Haiya Chemical Co., Ltd.; Jiang, Yueheng; Que, Limin; Xu, Jun; Qin, Dongguang; Cai, Tong; (17 pag.)CN105585534; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 118863-62-0, name is 3-(4-Bromophenyl)-1H-[1,2,4]triazole, molecular formula is C8H6BrN3, 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. category: Triazoles

Example 43 Preparation of 3-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C23) In a 500 mL flask, 3-(4-bromophenyl)-1H-1,2,4-triazole (20.0 g, 89.6 mmol), 1-iodo-4-(trifluoromethoxy)benzene (39.0 g, 135 mmol) were diluted with N,N-dimethylformamide and water (4:1, 100 mL). Then copper(I) iodide (15.3 g, 80.6 mmol), 8-hydroxyquinoline (8.50 g, 58.2 mmol) and cesium carbonate (87.4 g, 269 mmol) were added. The reaction was heated to 150 C. and stirred for 16 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and filtered through Celite. Brine solution was added to the filtrate and stirred for 15 minutes. The layers were separated and the aqueous layer further extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered, and concentrated. The resulting residue was purified by flash column chromatography using 15% ethyl acetate/petroleum ether as eluent to afford the title compound as a white solid (10.0 g, 29%): mp 100-103 C.; 1H NMR (300 MHz, DMSO-d6) delta 9.42 (s, 1H), 8.07 (d, J=9.0 Hz, 2H), 8.05 (d, J=9.0 Hz, 2H), 7.73 (d, J=8.4 Hz, 2H), 7.62 (d, J=8.4 Hz, 2H); ES+ m/z 385 ([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 118863-62-0, its application will become more common.

Reference:
Patent; Dow AgroSciences LLC; Baum, Erich W.; Fischer, Lindsey G.; Crouse, Gary D.; Sparks, Thomas C.; Giampietro, Natalie C.; Dent, III, William H.; Niyaz, Noormohamed M.; Petkus, Jeff; Demeter, David A.; Lambert, William Thomas; McLeod, CaSandra L.; Rigsbee, Emily Marie; Renga, James M.; (128 pag.)US2016/21883; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 7411-23-6, 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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows.

To a colorless solution of 3,5-dibromo-1H-1,2,4-triazole (lnt-1, 500 mg, 2.2 mmol) and 3-iodotetrahydrofuran (524 mg, 2.64 mmol) in DMF (3 ml) was added K2C03 (305 mg, 2.2 mmol). The vial was closed under Argon and stirred over night at 120C. The reaction mixture was diluted with 50 mL H20 and extracted with EtOAc (2 x 50 mL). The organic layers were washed with sat NaCl (3 x 50 mL), dried over MgS04 and concentrated in vacuo. The title compound was isolated as a white solid (619 mg, 2.08 mmol, 94.6 % yield). MS (ES+) m/z 297.9 [(M+H)+].

The chemical industry reduces the impact on the environment during synthesis 3,5-Dibromo-1H-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

15294-81-2, name is 4,5-Dibromo-1H-1,2,3-triazole, belongs to Triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C2HBr2N3

Iodomethane (1.819 mL, 29.1 mmol) was added cautiously to a suspension of 4,5- dibromo-lH-l,2,3-triazole (4.4 g, 19.40 mmol) and potassium carbonate (5.36 g, 38.8 mmol) in THF (20 mL) at room temperature. The resulting mixture was stirred overnight. The reaction was poured into water (50 mL) and extracted with ethyl acetate (3×100 mL). The combined organics were washed with brine (50 mL), dried over sodium sulphate, filtered and concentrated in vacuo. Purification was by silica gel chromatography (eluted with a 0-50% ethyl acetate/isohexane) to give 4,5-dibromo-l-methyl-lH-l,2,3-triazole as a white solid (M+H 239.7; LCMS method 2).

The synthetic route of 15294-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; NOVARTIS AG; TELLEW, John Edward; WANG, Xia; WAN, Yongqin; XIE, Yun Feng; PAN, Shifeng; JIANG, Jiqing; XIE, Yongping; HUNT, Thomas Anthony; EDWARDS, Lee; BEATTIE, David; HEALY, Mark Patrick; WEST, Ryan; LISTER, Andrew Stuart; WO2012/138648; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – 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 7411-23-6 as follows. SDS of cas: 7411-23-6

A Compound WX122-1 (4 g) was dissolved in DMF (100 ml) and the resulting solution was cooled down to0C. NaH (846.3mg) was added in batch. Gas was generated during the process, and after 0.5 hour, MeI (2.6 grams)was added dropwise into the reaction solution which was slowly heated to 25C namely room temperature and stirredfor 12 hours. The reaction solution was poured into a saturated ammonium chloride solution (300ml), and extracted withethyl acetate (50ml33), and the organic phase was washed with a saturated sodium chloride solution (100ml). Theorganic phases were mixed and dried with anhydrous sodium sulfate, filtered, and concentrated under the reducedpressure. This compound was used directly in the next step and did not require purification. ESI m/z: [M+H]+= 242.

According to the analysis of related databases, 7411-23-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Danhong Pharmaceutical Co., Ltd.; LUO, Zhi; LI, Xiaolin; YANG, Yaxun; YANG, Lele; LI, Peng; HE, Haiying; LI, Jian; CHEN, Shuhui; (155 pag.)EP3626699; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics