Month: May 2021

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. 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, A new synthetic method of this compound is introduced below., Safety of 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one

A mixture of 5-(chloromethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (30, 2.00 g, 15.0 mmol, synthesized by the method of Cowden et al. 59), (4-bromophenyl)methanethiol (3.04 g, 15.0 mmol), and K2CO3 (2.48 g, 18.0 mmol) in DMF (40 mL) was stirred at room temperature for 12 h. After H2O was added to the reaction mixture, the precipitated solid was collected and washed with H2O and diethyl ether to give the title compound as a white powder (3.97 g, 13.2 mmol, 88percent). 1H NMR (300 MHz, DMSO-d6) d 3.36 (2H, s), 3.70 (2H, s), 7.28 (2H, d, J = 8.3 Hz), 7.52 (2H, d, J = 8.3 Hz), 11.29 (1H, br s), 11.39 (1H, br s).

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; Nara, Hiroshi; Sato, Kenjiro; Kaieda, Akira; Oki, Hideyuki; Kuno, Haruhiko; Santou, Takashi; Kanzaki, Naoyuki; Terauchi, Jun; Uchikawa, Osamu; Kori, Masakuni; Bioorganic and Medicinal Chemistry; vol. 24; 23; (2016); p. 6149 – 6165;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 10570-40-8, name is 4-Methyl-4H-1,2,4-triazole, molecular formula is C3H5N3, 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. Safety of 4-Methyl-4H-1,2,4-triazole

A solution of 4-methyl-1,2,4-triazole (1:08 g, 13 mmol) and DNPH (2:60 g, 13 mmol) in CH2Cl2 (20 mL) was stirred at 20 C for 4 d. The product precipitated and was collected by filtration, washed with CH2Cl2 (5 mL) and Et2O (5 mL), and dried to yield 2.45 g (67%) of a yellow powder. – 1H NMR (300 MHz, [D6]DMSO): delta = 3:84 (s, 3H), 6.32 (d, J =9:7 Hz, 1H), 7.41 (s, 2H), 7.77 (dd, J = 9.7 Hz, J = 3.1 Hz, 1H), 8.59 (d, J = 3.1 Hz, 1H), 8.98 (s, 1H), 9.98 ppm. – 13C NMR (75 MHz, [D6]DMSO): delta = 34:1, 125.0, 126.5, 127.4, 136.0, 140.7, 143.4, 170:3 ppm. – IR (neat): nu = 3294 w, 3236 w, 3081 m, 2988 m, 1595 s, 1550 m, 1525 s, 1475 m, 1431 m, 1371 m, 1307 s, 1258 s, 1175 m, 1128 s, 983 m, 834 s, 710 m, 654 m, 618 s cm-1. – C9H10N6O5 (282.21): calcd. C 38.30, H 3.57, N 29.78; found C 38.28, H 3.42, N 29.40.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10570-40-8, its application will become more common.

Reference:
Article; Laus, Gerhard; Kahlenberg, Volker; Wurst, Klaus; Schottenberger, Herwig; Zeitschrift fur Naturforschung – Section B Journal of Chemical Sciences; vol. 69; 9-10; (2014); p. 950 – 964;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-70-2, A common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, 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.

1,2,3-Triazole-4-carboxylic acid (14 mg, 124 mumol), DIPEA (86.3 muL, 496 mumol) and HATU (47.1 mg, 124 mumol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid 2-morpholin-4-yl-2-oxo-ethyl ester (54 mg, 120 mumol). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product purified by preparative HPLC and lyophilized to yield the title compound (35 mg; purity 95%). MS m/z [M+H]+ calc’d for C28H33N5O6, 536.24. found 536.2.

The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE, INC.; US2012/213806; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 7170-01-6, A common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, molecular formula is C3H5N3, 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 93Preparation of 4-(3-methyl-1H-1,2,4-triazol-1-yl)benzaldehyde (DI53); To a stiffing solution of 4-fluorobenzaldehyde (5.0 g, 40.32 mmol) in DMF (50 mL), were added K2CO3 (3.34 g, 40.32 mmol) and 3-methyl-1,2,4-trizole (3.34 g, 40.32 mmol) and the resultant reaction mixture was stirred at RT for 4 h. After completion of the reaction (TLC), the reaction mixture was diluted with water and extracted with EtOAc (3×). The combined EtOAc layer was washed with water and brine then dried over Na2SO4 and concentrated under reduced pressure to afforded the title compound as a white solid (4.1 g, 60%): mp 125-128 C.; 1H NMR (400 MHz, CDCl3) delta 10.05 (s, 1H), 8.76 (s, 1H), 8.02 (d, 2H), 7.85 (d, 2H), 2.50 (s, 3H); ESIMS m/z 188.04 ([M+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; Hunter, James E.; Lo, William C.; Watson, Gerald B.; Patny, Akshay; Gustafson, Gary D.; Pernich, Dan; Brewster, William K.; Camper, Debra L.; Lorsbach, Beth; Loso, Michael R.; Sparks, Thomas C.; Joshi, Hemant; Mandaleswaran, Adiraj; Sanam, Ramadevi; Gundla, Rambabu; Iyer, Pravin S.; US2012/329649; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2, These common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic 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.

O. (2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid isobutyl ester (R4=H; R7=-CH2CH(CH3)2) (2S,4R)-4-Amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid (76 mg, 242 mumol) in MeCN (0.4 mL, 8 mmol) and 4 M HCl in 1,4-dioxane (242 muL, 969 mumol) was combined with 2-methyl-propan-1-ol (0.5 mL) at 60 C. The resulting mixture was stirred until solid precipitation was observed (~30 minutes). The solvent was evaporated under vacuum and the solids were azeotroped in toluene and dried under vacuum. 1,2,3-Triazole-4-carboxylic acid (0.0274 g, 0.242 mmol), DIPEA (169 muL, 969 mumol) and HATU (92 mg, 242 mumol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with the dried solids, predissolved in DMF (0.2 mL) and DIPEA (0.5 eq.). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product was purified by preparative HPLC and lyophilized to yield the title compound (36 mg; purity 95%). MS m/z [M+H]+ calc’d for C26H32N4O4, 465.24. found 465.4.

The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE, INC.; US2012/213806; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1186050-58-7, The chemical industry reduces the impact on the environment during synthesis 1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid, I believe this compound will play a more active role in future production and life.

General procedure: Exarm}le 69: 2-Fluoro-N-[(/5,25)-2-[(6-fluoro-l,3-benzotliiazol-2- yl)amino]cyclopentyl]-6-(2H-l,2,3-triazol-2-yl)benzamide To a solution of (iS,2S)-l-N-(6-fluoro-l,3-benzothiazol-2-yl)cyclopentane-l,2-diamine hydrochloride (Intermediate 16a, 50 mg, 0.174 mmol) in dry DCM (2 ml) was added 2- fluoro-6-(2H-l,2,3-triazol-2-yl)benzoic acid (Intermediate 21, 54.0 mg, 0.261 mmol), triethylamine (0.073 ml, 0.521 mmol) and HATU (99 mg, 0.261 mmol). The reaction was stirred at room temperature for 18 hours then diluted with DCM, washed with water, filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by reverse phase preparative HPLC (acetonitrile / water with 0.1% ammonia) to afford the title compound.1H NMR (400 MHz, MeOD -d4) : delta ppm 1.56 – 1.72 (m, 2 H), 1.75 – 1.89 (m, 2 H), 2.16 – 2.32 (m, 2 H), 4.09 – 4.18 (m, 1 H), 4.22 – 4.31 (m, 1 H), 6.93 – 7.02 (m, 1 H), 7.19 – 7.30 (m, 2 H), 7.33 – 7.40 (m, 1 H), 7.53- 7.62 (m, 1 H), 7.74 (s, 2 H), 7.76 – 7.80 (m, 1 H) MS ES+: 441

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, 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 288-36-8, 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 288-36-8 as follows.

1, 2, 3-Triazole (3.45 g, 50 mmol) , 2-iodo-5-methylbenzoic acid (5.24 g, 20 mmol) , cesium carbonate (11.72 g, 36 mmol) , trans-N, N’-dimethyl-1, 2-cyclohexanediamine (0.51 g, 3.60 mmol) , cuprous iodide (0.38 g, 2 mmol) and N, N-dimethylformamide (30 mL) were added sequentially to a 100 mL of single-necked round-bottomed flask under nitrogen, and the mixture was warmed gradually to 100 and reacted for 4 h. The reaction mixture was cooled, diluted with water, and extracted with ethyl acetate (200 mL x 2) . The aqueous layer was acidified to pH 12 with concentrated hydrochloric acid, and the resulting mixture was extracted with ethyl acetate (200 mL x 2) . The combined organic layers were dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel eluted with (dichloromethane/methanol (v/v) 50/1) to give the title compound (as a yellow solid, 2.76 g, 68) .[MS (ESI, neg. ion) m/z: 202.1 [M-H]- and1H NMR (CD3OD, 600 MHz) delta (ppm) : 7.88 (s, 2H) , 7.66 (d, 1H) , 7.59 (d, J 8.2 Hz, 1H) , 7.507.48 (dd, J 8.1 Hz, 1.1 Hz, 1H) , 2.45 (s, 3H) .13C NMR (CD3OD, 151 MHz) delta (ppm) : 169.8, 140.7, 137.5, 136.7, 133.5, 131.5, 129.3, 126.0, 21.0.

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; GAO, Jinheng; ZHANG, Ji; (107 pag.)WO2017/12502; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7411-23-6, 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.

In a 250 mL round bottomed flask sodium hydride (60% dispersion in mineral oil) (132 mg, 3.31 mmol) was added to a colorless solution of 3,5-dibromo-1H-1,2,4-triazole (Int-1, 500 mg, 2.2 mmol) in DMF (10 ml). The resulting suspension was stirred at room temp during 30 min and trideuterio(iodo)methane (319 mg, 2.2 mmol) was added and the reaction was stirred at 40C over night.The reaction mixture was poured into 50 mL H20 and extracted with EtOAc (3 x 50 mL). The organic layers were washed with sat NaCl (3 x 50 mL), dried over MgSO4 and concentrated in vacuo. The title compound was isolated as an off-white solid (456 mg, 84.8 % yield). MS (ES+) m/z: 244.9 [(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

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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., name: 1H-[1,2,3]Triazole-4-carboxylic acid

lH-l,2,3-triazole-5-carboxylic acid (1.1 mg, 10.0 muiotaetaomicron) was combined with HATU (3.0 mg, 7.8 muiotaetaomicron) in DMF (0.5 mL) and stirred for 10 minutes; DIPEA (1 eq.) was added and the mixture was stirred for 1 minute. Compound 2 (5.0 mg, 11 muiotaetaomicron) was dissolved in DMF (1 mL) and DIPEA (5.8 mu^, 33 muiotaetaomicron) was added, followed by addition of the activated acid solution. yield Compound 3.

According to the analysis of related databases, 16681-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FLEURY, Melissa; BEAUSOLIEL, Anne-Marie; HUGHES, Adam D.; LONG, Daniel D.; WILTON, Donna A.A.; WO2015/116786; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 288-36-8,Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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.

To a mixture of the product from step 2 (7.9 g, 38 mmol), cesium carbonate (24.8 g,76 mmol) and CuI (2.88 g, 7.6 mmol) in DMF (200 mL) were added 2H-[1,2,3]triazole (5.24 g,76 mmol) and N,N’-dimethyl-cyclohexane-1,2-diamine (0.9 g, 6.5 mmol) and the mixture was heated to 110 C overnight. The cooled reaction mixture was adjusted to ~pH 12 with IM sodium hydroxide and extracted with EtOAc (50 mL x 3). The aqueous layer was adjusted to ~pH 4 with IM HCl and extracted with EtOAc (50 mLx4). The extracts was dried over Na2S04, filtered, the filtrate concentrated in vacuo and the residue purified by chromatography on silica (Petroleum ether : EtOAc =10: 1) to provide the title compound (4.1 g). LRMS m/z (M+H) 196.0 found, 196.0 required.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; BESHORE, Douglas, C.; KUDUK, Scott, D.; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/20930; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics