Tag: M.W:200-300

These common heterocyclic compound, 28938-17-2, name is 4,5-Dibromo-2-methyl-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. HPLC of Formula: C3H3Br2N3

Intermediate 14d (0551) 5-Bromo-2-methyl-2H- 1 ,2,3-triazole-4-carboxylic acid (0552) A solution of 4,5-dibromo-2-methyl-2H-l,2,3-triazole (Intermediate 14e; 144 g, 597.81 mmol) in anhydrous THF (1.5 L) was cooled to -30 C under nitrogen atmosphere and i- PrMgCl (330 mL, 658 mmol, 2M in THF) was added dropwise. The solution was stirred at -30 C for 1 hour, and then bubbled with C02 for 3 hours at <10 C. The reaction was then stirred at 25 C for 16 hours. The mixture was quenched with aqueous HC1 (-3000 mL, 0.1M) to pH = ~2 and extracted with EtOAc (3 L x 3). The organic phase was then extracted with aqueous NaOH (0.1M, 2 L x 3). The aqueous phase was then added to aqueous HC1 (~6 L, 0.1M) to pH=~2 and extracted with EtOAc (3L x 3). The organic phase was dried with Na2S04 and concentrated under vacuum to give 5-bromo-2-methyl- 2H-l,2,3-triazole-4-carboxylic acid (Intermediate 14d; 105 g, 85.26% yield) as a white solid. lH NMR (DMSO, 400 MHz) delta 4.23 (s, 3H). 13C-NMR (400MHz, DMSO) delta 160.86, 138.23, 124.52, 43.38. The synthetic route of 4,5-Dibromo-2-methyl-2H-1,2,3-triazole has been constantly updated, and we look forward to future research findings. Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; FERON, James, Lyman; (80 pag.)WO2017/80980; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 217448-86-7,Some common heterocyclic compound, 217448-86-7, name is Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate, molecular formula is C11H9F2N3O2, 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 6: Preparation of Rufinamide Methyl l-(2, 6-difIuorobenzyl)-lH-l,2,3-triazole- 4-carboxylate (19 g) was dissolved in methanol (285 ml) at 65-70C. Added dropwise 20% liq NH3 (150 ml) over a period of 30 min. The mixture was then stirred at 65-70C for 5-6 hours. After the completion of reaction, as monitored by TLC, the reaction mixture was cooled to room temperature. The solid was filtered, washed with water and dried under vacuum at 65C to give rufinamide (13.3 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate, its application will become more common.

Reference:
Patent; AARTI INDUSTRIES LIMITED; DESAI, Parimal, Hasmukhlal; SALVI, Narendra, Jagannath; SUBRAMANIAN, Seetharaman; WO2014/72992; (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 138624-97-2 as follows. category: Triazoles

A mixture of 7-amino-i ,5-dimethyl- 8 ,9-dthydro-7H-pyrido [3,2-b] azepine-2,6-dione(20 mg, 0.09 mmol), i-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (26 mg,0.14 mmol), 1 -hydroxybenzotriazole (18.3 mg, 0.14 mmol) and 1 -benzyl- 1 ,2,4-triazole-3-carboxylic acid (22 mg, 0.11 mmol) in N,N-dimethylformamide (1 mL) was stuffed at 25 Cfor 12 h. The mixture was concentrated under reduced pressure. The residue was purified byRP-HPLC (acetonitrile 20-50%/0.05% ammonium hydroxide in water) to afford the racemicmaterial (30 mg), which was separated by chiral SFC to give arbitrarily assigned:1 -benzyl-N- [(7R)- 1 ,5-dimethyl-2,6-dioxo- 8 ,9-dihydro-7H-pyrido [3,2-b] azepin-7-yl] – i,2,4-triazole-3-carboxamide (Peak 1, retention time 2.38 mm) (8.1 mg, 25%) as white solids.?H NMR (400 MHz, CD3OD) oe 8.56 (s, 1H), 7.58 (d, J = 10.0 Hz, 1H), 7.36 – 7.34 (m, 5H),6.57 (d, J = 9.2 Hz, 1H), 5.47 (s, 2H), 4.67 – 4.62 (m, 1H), 3.68 (s, 3H), 3.29 (s, 3H), 3.06 -3.05 (m, 1H), 2.88 – 2.84 (m, 1H), 2.75 – 2.72 (m, 1H), 2.27 – 2.22 (m, 1H). LCMS RT =0.695 mm, mlz = 407.1 [M + H]. LCMS (5 to 95% acetonitrile in water + 0.03%trifluoacetic acid over 1.5 mins) retention time 0.695 mi ESI+ found [M+H] =407.1.1 -benzyl-N-[(7S)- 1 ,5-dimethyl-2,6-dioxo-8,9-dihydro-7H-pyrido[3,2-b] azepin-7-yl] -i,2,4-triazole-3-carboxamide (Peak 2, retention time 3.639 mm) (5.3 mg, 17%) as white solids. ?H NMR (400 MHz, CD3OD) oe 8.56 (s, 1H), 7.58 (d, J = 9.6 Hz, 1H), 7.37 – 7.33 (m, 5H), 6.57 (d, J = 10.0 Hz, 1H), 5.47 (s, 2H), 4.67 – 4.62 (m, 1H), 3.68 (s, 3H), 3.29 (s, 3H),3.10 – 3.05 (m, 1H), 2.88 – 2.86 (m, 1H), 2.75 – 2.72 (m, 1H), 2.27 – 2.22 (m, 1H). LCMS RT = 1.202 mi mlz = 407.2 [M + H]. LCMS (10 to 80% acetonitrile in water + 0.05%ammonium hydroxide over 3 mins) retention time 1.202 mi ESI+ found [M+H] = 407.2. SFC condition: Column: Chiralpak AD-3 100×4.6mm I.D., 3um Mobile phase: A:C02 B: methanol (0.05% DEA) Gradient: from 5% to 40% of B in 5mm and hold 40% for 2.5 mm, then 5% of B for 2.5 mm Flow rate: 2.8mL/min Column temp.: 40 C.

According to the analysis of related databases, 138624-97-2, the application of this compound in the production field has become more and more popular.

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

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. 118863-62-0, name is 3-(4-Bromophenyl)-1H-[1,2,4]triazole, A new synthetic method of this compound is introduced below., Formula: C8H6BrN3

Example 243 (S)-2-((1-(4-(1H-1,2,4-Triazol-3-yl)phenyl)-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]inden-4-yl)oxy)propanamide 243 243 was prepared using commercially available 3-(4-bromophenyl)-1H-1,2,4-triazole and following procedures analogous to those of Example 242. LCMS (ESI): RT (min)=1.02, [M+H]+=419, method=F; 1H NMR (300 MHz, DMSO-d6) delta 12.28 (br, 1H), 8.53 (s, 1H), 8.20 (d, J=8.4 Hz, 2H), 7.82 (d, J=8.4 Hz, 2H), 7.55 (s, 1H), 7.25 (s, 1H), 6.94 (d, J=2.1 Hz, 1H), 6.62 (d, J=2.1 Hz, 1H), 4.67-4.60 (m, 1H), 4.44-4.40 (m, 2H), 4.27-4.24 (m, 2H), 2.20-2.00 (m, 2H), 1.80-1.55 (m, 2H), 1.45 (d, J=6.6 Hz, 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

Reference 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.

a. A solution of 1.72 g (43 mmol) of sodium hydroxide in 2 mL of water was added with stirring to a solution of 10.0 g (43 mmol) of triazole 1 in 100 mL of DMF, and 6.49 g (43 mmol) of isopentyl bromide was then added. The mixture was stirred for 13 h on a boiling water bath, cooled, and poured into 1 L of water. The yellow oily material was separated using a separatory funnel (bottom layer), additionally washed with water, and dried for 3 days in a vacuum desiccator over phosphoric anhydride. The product was used in further syntheses without additional purification. Yield 11.5 g (89 %).

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:
Article; Tolstyakov; Russian Journal of Organic Chemistry; vol. 54; 10; (2018); p. 1537 – 1547; Zh. Org. Khim.; vol. 54; 10; (2018); p. 1525 – 1534,10;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1157938-97-0, 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. 1157938-97-0 name is 1-(2,5-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, 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.

A 2-neck flask was charged with zinc (5.8 g, 89 mmol, 2.0 eq.) under a nitrogen atmosphere and anhydrous THF (101 mL) and then trimethylsilylchloride (TMSC1, 1.12 mL) were added. The resulting suspension was stirred at room temperature for 30 minutes and then cooled to 0 C. Subsequently, ethyl-2-bromopropionate (5.8 mL, 8.1 g, 44.7 mmol, 1.0 eq.) was dosed to the suspension in a drop wise fashion over 30 minutes. The reaction mixture was stirred for an additional 15 minutes and then filtered under a nitrogen atmosphere into a Schlenk vessel to remove residual zinc. Ketone III (Ri = F, 1.0 g, 4.5 mmol, 1.0 eq.) was charged into a Schlenk vessel and anhydrous THF (10 mL) was added under a nitrogen atmosphere. To the resulting solution was added 20 mL of the previously prepared stock solution of Reformatsky reagent (vide supra, 8.36 mmol, 1.9 eq.) in a dropwise fashion over 30 minutes at room temperature while stirring. After completion of the addition the resulting reaction mixture was stirred under a nitrogen atmosphere for 36 hours (clear solution). GC-analysis showed that the ester I (Ri = F) had formed with 80% conversion based on ketone III (Ri = F) and a d.e. of 60% in favor of the desired RR/SS diastereomer. The reaction mixture was concentrated in vacuo to a volume of 10 mL after which w-heptane was added until formation of a solid was observed. The resulting suspension was stirred for 16 hours after which the solid was isolated through filtration. The solid was then dissolved in a mixture of aqueous HC1 (pH = 1) and ethyl acetate resulting in a clear biphasic system. The phases were separated and the aqueous layer was extracted with ethyl acetate (2x). The combined organic layers were washed with water and brine, dried (Na2S04), filtered and concentrated in vacuo to give racemic RR/SS ester I (Ri = F) as a light yellow solid with > 99% d.e. as determined by GC.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2,5-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; BASILEA PHARMACEUTICA AG; VAN SUMMEREN, Ruben; VAESSEN, Harrie; MINK, Daniel; WASER, Mario; WO2014/23623; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

138624-97-2, name is 1-Benzyl-1H-1,2,4-triazole-3-carboxylic 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. SDS of cas: 138624-97-2

M-30 (25 mg) was dissolved in 2 mL of dichloromethane and 1 mL of trifluoroacetic acid, and after 1 hour of reaction, the solvent was spin-dried to obtain the intermediate amine. Subsequently, the intermediate was dissolved in DMSO (1 mL), and 35 mg of acid-6 was added (the acid was purchased commercially, or the preparation of the acid please refer to: CN 105121432 A, J. Med. Chem. 2017, 60, 1247 ), HATU (56mg), DIPEA (60 mg), the reaction was overnight, added water and ethyl acetate extraction, the organic layer was collected, dried over anhydrous sodium sulfate, vacuum rotary evaporation to remove the solvent, HPLC separation to obtain compound ZB-R-24.

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

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhou Bing; Tang Wei; Yang Xiangbo; Lu Huimin; Gao Mengying; Yang Yaxi; Feng Huijin; (69 pag.)CN111138448; (2020); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route 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.

Intermediate 5 3,5-dibromo-l-(2-methylpropyl)-lH-l,2,4-triazole Sodium te/t-butoxide (699 mg, 7.27 mmol) was added to a solution of 3,5-dibromo-l/-/-l,2,4- triazole (1.5 g, 6.61 mmol) in DMF (10 mL). The mixture was stirred at rt for 10 minutes. 1- Bromo-2-methylpropane (0.8 mL, 7.27 mmol) was added and the mixture was heated at 50C for 4 h and let to rt. Water (100 mL) was added and the mixture was extracted with EtOAc (2 x 50 mL). The organic phase was washed with brine (50 mL) and dried over sodium sulfate and concentrated to give the title compound as a liquid (1.47 g, 79%). XH NMR (400 MHz, CDCI3): delta ppm 0.94 (d, 6 H), 2.21 – 2.32 (m, 1 H), 3.93 (d, 2 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; ACTURUM LIFE SCIENCE AB; BESIDSKI, Yevgeni; YNGVE, Ulrika; PAULSEN, Kim; LINDE, Christian; MALMBORG, Jonas; WO2014/195322; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – 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. 15294-81-2, name is 4,5-Dibromo-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C2HBr2N3

Example 121: Preparation of 4,5-dibromo-l-methyl-lH-[l,2,3″|triazole and 4,5-dibromo- 2-methyl-2H-[l .2.31triazole(A) (B) To a solution of 4,5-dibromo- IH-[1, 2,3]triazole (2.26 g, 10 mmol) (Example 120) and triethyl amine (1.5 ml, 10 mmol) in dichloromethane (50 ml), was added methyl iodide (625 mul, 10 mmol). The reaction mixture was stirred at room temperature for 24 hours. More triethyl amine (0.75 ml, 5 mmol) and more methyl iodide (312 mul, 5 mmol) were added and the mixture was stirred for 3 hours. The reaction mixture was quenched by addition of aqueous ammonium chloride (saturated) (15 ml). The phases were separated and the organic phase was dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: 10-30% ethyl acetate in hexane) to give 4,5-dibromo-2-methyl-2H-[l,2,3]triazole (isomer B) (625 mg, 26% yield) and 4,5-dibromo- 1 -methyl- IH-[1, 2,3]triazole (isomer A) (825 mg, 34% yield).Isomer A 1H-NMR (400 MHz, CDCl3): 4.09 (s, 3H, Me) ppm. Isomer B 1H-NMR (400 MHz, CDCl3): 4.18 (s, 3H, Me) ppm.

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 15294-81-2.

Reference:
Patent; SYNGENTA LIMITED; WO2007/96576; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 7411-23-6, These common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-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.

2-(3-bromopropoxy)tetrahydro-2H-pyran (5.60 g, 4.25 ml, 25.1 mmol, Eq: 1.00) and DIPEA (3.24 g, 4.38 ml, 25.1 mmol, Eq: 1.00) were added to a suspension of 3,5-dibromo-lH- 1,2,4- triazole (5.69 g, 25.1 mmol, Eq: 1.00) in MeCN (50.0 ml). The reaction was stirred at 90 C for 3 hr, cooled down to RT and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel (eluent: EtOAc/ heptane from 20/80 to 60/40) to yield 3, 5-dibromo-l-(3-tetrahydropyran- 2- yloxypropyl)- 1,2, 4-triazole (7.50 g, 19.7 mmol, 79% yield) as light yellow oil.

Statistics shows that 3,5-Dibromo-1H-1,2,4-triazole is playing an increasingly important role. we look forward to future research findings about 7411-23-6.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; RATNI, Hasane; CARTER, Jennifer Louise; (54 pag.)WO2020/48904; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics