Tag: M.W:200-300

Synthetic Route of 217448-86-7, 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. 217448-86-7, name is Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A 250 mL two-necked round bottomflask was charged with sodium azide (6.10 g, 93.8 mmol), compound2 (1.90 g, 6.84 mmol), and water (20 mL). After the solidwas completely dissolved, compound 1a (5.0 g, 31.37 mmol) andCH3CN (80 mL) were added. The mixture was stirred at room temperaturefor 3 h, and then the CH3CN layer was separated. To theCH3CN solution were added Cu2O-NP (0.42 g) and compound 4(2.80 mL, 31.3 mmol), and the reaction mixture was stirred for8 h at room temperature under protection of inert gas. The mixturewas filtered and the filtrate was concentrated, and was chargedwith methanol (40 mL) and 35% ammonia in water (100 mL). The mixture was heated to 65 C and refluxed for 4 h, cooled to roomtemperature, and filtered. The resulting solid was washed withwater and methanol to obtain rufinamide (5.25 g, 71.6%) as colorlesscrystalline product. Mp: 242-244 C. 1H NMR (400 MHz,DMSO-d6) d 8.549 (s, 1H), 7.842 (br s, 1H), 7.566-7.470 (m, 2H),7.215-7.174 (m, 2H), 5.723 (s, 2H). 13C NMR (100 MHz, DMSOd6)d 162.5, 161.7, 160.0, 143.3, 132.3, 127.4, 112.4, 111.5, 41.66.MS (ESI+): 239.06.

The chemical industry reduces the impact on the environment during synthesis Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Jing-Han; Pan, Cheng-Wen; Li, Yong-Tao; Meng, Fan-Fei; Zhou, Hong-Gang; Yang, Cheng; Zhang, Quan; Bai, Cui-Gai; Chen, Yue; Tetrahedron Letters; vol. 54; 26; (2013); p. 3406 – 3409;,
1,2,3-Triazole – Wikipedia,
Triazoles – 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. 138624-97-2, name is 1-Benzyl-1H-1,2,4-triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9N3O2

A mixture of 1-benzyl-1H-1,2,4-triazole-3-carboxylic acid (32 mg, 0.16 mmol), 1-(3- dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (28 mg, 0.14 mmol), 3-amino-i – methyl-4,5-dihydro-3h-pyrido [1,2-a] [1,3] diazepine-2,7-dione (25 mg, 0.12 mmol) and 1- hydroxybenzotriazole (20 mg, 0.14 mmol) in N,N-dimethylformamide (3 mL) was stuffed at 25 C for 12 h. The mixture was concentrated to dryness under reduce pressure. The resultingresidue was purified by reverse phase chromatography (acetonitrile 10-40% / 0.05% ammonia hydroxide in water) to afford 1 -benzyl-N-( 1 -methyl-2,7-dioxo- 1,2,3,4,5,7- hexahydropyrido [1,2-a] [1,3] diazepin-3-yl)- 1 H-i ,2,4-triazole-3-carboxamide (30 mg, 63%) as a white solid. The racemic material was further purified by SFC to give arbitrarily assigned:1 -benzyl-N-[(3S)- 1 -methyl-2,7-dioxo-4,5-dihydro-3H-pyrido[ 1,2-a] [1 ,3]diazepin-3-yl]-1,2,4-triazole-3-carboxamide (Peak 1, retention time = 5.180 mm) (12 mg, 40%) as white solids. ?H NMR (400 MHz, CD3OD) 5 8.57 (s, 1H), 7.64 – 7.56 (m, 1H), 7.47 – 7.25 (m, 5H), 6.53 (d, J = 9.2 Hz, 1H), 6.46 (d, J = 7.2 Hz, 1H), 5.47 (s, 2H), 5.07 – 5.03 (m, 1H),4.61 – 4.55 (m, 1H), 3.71 – 3.63 (m, 1H), 3.39 (s, 3H), 2.68 – 2.60 (m, 1H), 2.19 – 2.12 (m, 1H). LC-MS RT = 1.177 mm, mlz = 393.2 [M+H]. LCMS (10 to 80% acetonitrile in water +0.03% ammonium bicarbonate over 3.0 mins) retention time 1.177 mm, ESI+ found [M+H] =393.2.1 -benzyl-N- [(3R)- 1 -methyl-2,7-dioxo-4,5-dihydro-3H-pyrido [1,2-a] [1,3] diazepin-3-yl]-1,2,4-triazole-3-carboxamide. (Peak 2, retention time = 6.616 mm) (8 mg, 26%) as white solids. ?H NMR (400 MHz, CD3OD) (5 8.56 (s, 1H), 7.63 – 7.57 (m, 1H), 7.43 – 7.25 (m, 5H), 6.52 (d, J = 9.2 Hz, 1H), 6.45 (d, J = 7.2 Hz, 1H), 5.47 (s, 2H), 5.06 – 5.01 (m, 1H),4.59 – 4.56 (m, 1H), 3.69 – 3.62 (m, 1H), 3.39 (s, 3H), 2.68 – 2.60 (m, 1H), 2.19 – 2.12 (m, 1H). LC-MS RT = 1.179 mi mlz = 393.1 [M+Hf?. LCMS (10 to 80% acetonitrile in water +0.03% ammonium bicarbonate over 3.0 mins) retention time 1.179 mi ESI+ found [M+H] =393.1.SFC condition: column: chiralcel OD-3 100 x 4.6mm I.D., 3um mobile phase:A:C02 B: ethanol (0.05% DEA) gradient: hold 5% for 1.0 mm, then from 5% to 40% of B in 4.5 mm and hold 40% for 2.5 mm, then 5% of B for 1.0 mm. Flow rate: 2.8 mL/min. Columntemperature: 40 C.

The synthetic route of 138624-97-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; (105 pag.)WO2018/73193; (2018); A1;,
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. 74733-90-7, name is 2-(4-Bromophenyl)-2H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. category: Triazoles

Step 5. 2-(4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)-2H-1 ,2,3- triazole. [1.1.5d] A microwave vial was charged with 1.1.5c (1.66 g, 7.41 mmol) and 1 ,4-dioxane (60 mL). KOAc (2.254 g, 22.97 mmol) and bis(pinacolato)diboron (2.258 g, 8.89 mmol) were added and the mixture was purged with N2 for 5 minutes. PdCI2(dppf).CH2CI2 adduct (0.605 g, 0.741 mmol) was then added and the reaction mixture was stirred at 68 C for 5 hours. The mixture was diluted with EtOAc and stirred with Siliabond DMT overnight, then washed with water, brine, dried filtered and evaporated onto silica gel. Purification by flash column chromatography on silica gel (EtO Ac/Heptane, 0 to 40%) afforded product 1.1.5d (1.38 g, 68.7 % yield) as an off white solid. LCMS (m/z) 272.2 [M+H]+ 1H NMR (400 MHz, CDCI3) delta 8.10 (d, J = 8.61 Hz, 2H), 7.94 (d, J = 8.22 Hz, 2H), 7.81 – 7.86 (m, 2H), 1.34 – 1.42 (m, 12H)

The synthetic route of 74733-90-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FU, Jiping; KARUR, Subramanian; MADERA, Ann Marie; PECCHI, Sabina; SWEENEY, Zachary Kevin; TJANDRA, Meiliana; YIFRU, Aregahegn; WO2014/160649; (2014); 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. Quality Control of 3,5-Dibromo-1H-1,2,4-triazole

To a solution of 3,5-dibromo-1H-1,2,4-triazole (Int-1, 5.0 g, 22.0 mmol) in DMF (70 mL) was added sodium hydride (793 mg, 33.1 mmol) at 0C under argon atmosphere. After complete addition reaction was allowed to stir at 25C for 30 min. Then 2-iodopropane (2.6 mL, 26.4 mmol) was added followed by stirring at 40C for 4 h. After complete consumption of starting material (as monitored by TLC) reaction mixture was poured into ice-water followed by extraction with MTBE. The organic layer was separated and dried over sodium sulphate. Solvent was evaporated under reduced pressure to afford the title compound as yellow liquid (5.4 g, crude) which was sufficiently pure for use in next step. 1H NMR (DMSO-d6, 400 MHz): 1.39 (d, J = 6.6 Hz, 6 H), 4.64-4.71 (m, 1 H). MS (ES+) m/z 270.0 [M+H].

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; 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

Adding a certain compound to certain chemical reactions, such as: 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, belongs to triazoles 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 7411-23-6, Product Details of 7411-23-6

In a 100 mL round bottomed flask, 3,5-dibromo-1H-1,2,4-triazole (Int-1, 500.0 mg, 2.2 mmol) was dissolved in DMF (32 mL) and the solution was cooled to 0-5 C (ice bath). Sodium hydride (55% dispersion in mineral oil, 106 mg, 2.64 mmol) was added in portions and the resulting mixture was stirred for 5 min at 0-5 C and for 15 min at room temperature. After that, 2-methoxyethyl methanesulfonate (815.5 mg, 5.29 mmol) was added dropwise at room temperature. The resulting mixture was stirred for 15 h at room temperature. After that, it was diluted with ethyl acetate (20 mL) and water (20 mL), the aqueous phase was extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo, the residue was purified by column chromatography (silica gel, 30 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 20:80 v/v) to yield the title compound as colorless oil (362 mg, 58%). 1H NMR (CDC13, 300 MHz): 3.33 (s, 3 H), 3.76 (t, J = 5.3 Hz, 2 H), 4.29 (t, J = 5.3 Hz, 2 H). MS (ES+) m/z 285.8.

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, 3,5-Dibromo-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

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

Reference of 23579-79-5,Some common heterocyclic compound, 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, molecular formula is C3H3Br2N3, 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.

In a 50 mL pressure vial, 3,5-dibromo-1-methyl-1H-1,2,4-triazole (Int-41, 1.42 g, 5.89 mmol) was dissolved in DMF (12 mL) and potassium carbonate (1.36 mg, 9.82 mmol), followed by 3- chloro-5-methylphenol (700 mg, 4.91 mmol) were added. The vial was sealed, the reaction mixture was stirred for 15 h at 100 C. After cooling, it was concentrated in vacuo, the residue was purified by column chromatography (silica gel, 70 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 25:75 v/v) to yield the title compound as white solid (1.37 g, 92%). 1H NMR (CDC13, 300 MHz): delta 2.37 (s, 3 H), 3.77 (s, 3 H), 6.99-7.02 (m, 1 H), 7.06-7.08 (m, 1 H), 7.11- 7.14 (m, 1 H). MS (ES+) m/z 302.0, 304.0, 306.0 [M+H, Br & CI isotopes] .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, its application will become more common.

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

Application of 1186050-58-7, These common heterocyclic compound, 1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid, 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.

Example 102 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide To a solution of (1S,2S)-1-N-[5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 1; 1.09 g, 3.87 mmol) in DCM (13 ml) was added 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1186050-58-7; 0.802 g, 3.87 mmol), DIPEA (2.027 ml, 11.61 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (0.579 g, 4.26 mmol) and EDC (0.816 g, 4.26 mmol). The reaction was stirred at room temperature for 17 hours and was then partitioned between DCM and a saturated solution of sodium bicarbonate, filtered through a hydrophobic fit and concentrated in vacuo. The residue was purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol) and re-crystallised from IPA to afford the title compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.41-1.59 (m, 2H), 1.59-1.76 (m, 2H), 1.95-2.10 (m, 2H), 4.06-4.20 (m, 2H), 6.68 (d, J=8.8 Hz, 1H), 7.29-7.41 (m, 2H), 7.57-7.66 (m, 2H), 7.71-7.75 (m, 1H), 8.00 (s, 2H), 8.25-8.28 (m, 1H), 8.63 (d, J=6.8 Hz, 1H) MS ES+: 435

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; Fieldhouse, Charlotte; Glen, Angela; Maine, Stephanie; Fujimoto, Tatsuhiko; Robinson, John Stephen; US2015/232460; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 22300-52-3, These common heterocyclic compound, 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole, 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 a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1?3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5?10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C?N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

The synthetic route of 22300-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 118863-62-0,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.

1.5 g of 3 -(4-bromophenyl)- 1H- 1,2, 4-triazole prepared in Step 2 was dissolved in 5.0 mL of N,N-dimethylformamide, and the resulting reaction mixture was cooled to 0C. To the reaction mixture, 0.32 g of sodium hydride was added, and then the reaction mixture was stirred for 30 minutes. 1.67 g of (2-(chloromethoxy)ethyl)trimethylsilane was added thereto and the reaction mixture was then stirred at 0C for 15 minutes and additionally stirred for 2 hours further. Distilled water was added and the reaction mixture was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give a residue as a yellow liquid. The residue was purified with silica gel column chromatography (developing solvent: n-hexane/ethyl acetate = 2/1) to give 1.1 g of the title compound as a yellow solid (yield: 46.3 %). 1H-NMR (CDCl3, 400 MHz) d 8.25(s, 1H), 8.0l(d, 2H), 7.58(d, 2H), 5.52(s, 2H), 3.69(t, 2H), 0.96(t, 2H), 0.00(s, 9H)

The synthetic route of 118863-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; HAN, Tae Dong; TAK, Hee Jae; KIM, Eun Kyung; CHOI, Su Bin; KIM, Dong Hoon; PARK, Sol; JUNG, Eun Hye; CHOI, Hyun Ho; KIM, Tae Wang; JU, Mi Kyeong; HA, Na Ry; (305 pag.)WO2019/180644; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 118863-62-0, A common heterocyclic compound, 118863-62-0, name is 3-(4-Bromophenyl)-1H-[1,2,4]triazole, molecular formula is C8H6BrN3, 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.

Example 221 (S)-1-(1-(4-(1H-1,2,4-Triazol-3-yl)phenyl)-8,9-dihydro-7H-6-oxa-2,9a-diazabenzo[cd]azulen-4-yl)pyrrolidine-2-carboxamide 221 221 was prepared using commercially available 3-(4-bromophenyl)-1H-1,2,4-triazole and following procedures analogous to those of Example 158. LCMS: RT (min)=3.00, [M+H]+=430, method=C; 1H NMR (300 MHz, DMSO-d6) delta 14.22 (s, 1H), 8.68 (s, 1H), 8.17 (d, J=8.1 Hz, 2H), 7.90 (d, J=7.8 Hz, 2H), 7.31 (d, J=2.3 Hz, 1H), 7.03 (s, 1H), 6.37 (d, J=2.1 Hz, 1H), 6.09 (d, J=2.1 Hz, 1H), 4.37-4.29 (m, 4H), 3.90-3.80 (m, 1H), 3.70-3.60 (m, 1H), 3.30-3.08 (m, 1H), 2.35-2.15 (m, 3H), 2.09-1.87 (m, 3H).

The synthetic route of 118863-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Braun, Marie-Gabrielle; Garland, Keira; Hanan, Emily; Purkey, Hans; Staben, Steven T.; Heald, Robert Andrew; Knight, Jamie; Macleod, Calum; Lu, Aijun; Wu, Guosheng; Yeap, Siew Kuen; (183 pag.)US2018/65983; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics