Day: February 10, 2021

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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 288-36-8

To a mixture of the product from Step 2 (7.9 g, 38 mmol) , Cs2CO3 (24.8 g, 76 mmol) , and CuI (2.88 g, 7.6 mmol) in DMF (200 mL) was 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 stirred at 110 overnight. The cooled mixture was adjusted topH 12 with 1 N sodium hydroxide and extracted with EtOAc (50 mL x 3) . The aqueous layer was adjusted topH 4 with 1 N HCl and extracted with EtOAc (50 mLx4) . The extracts were dried over Na2SO4, filtered, the filtrate concentrated in vacuo, and the residue was purified by silica gel column chromatography (petroleum ether: EtOAc10: 1) to provide the title compound. LRMS m/z (M+H) 196.0 found, 196.0 required.

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 288-36-8.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; (59 pag.)WO2016/101118; (2016); 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 40253-47-2 as follows. Recommanded Product: Ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate

A mixture of ethyl 5-methyl-lH-l ,2,4-triazole-3-carboxylate (1.0 g, 6.45 mmol) and sodium hydroxide (1.702 mL, 32.2 mmol) in tetrahydrofuran (30 mL) was stirred at ambient temperature for 16 hours. Volatiles were removed, and the residue was acidified with 1 N HQ solution. Water was removed under high vacuum, and the crude residue was purified by HPLC (0-70% acetonitrile in 0.1 % trifluoroacetic acid/water on Phenomenex C18 10 mupiiota (250 mm x 50 mm) column at a flowrate of 50 mL/minute) to give 460 mg of the title compound as a white solid.

According to the analysis of related databases, 40253-47-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 103755-58-4, A common heterocyclic compound, 103755-58-4, name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, molecular formula is C9H9N3O, 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 12: (R)-3-(l-Phenyl-cycloheptanecarbonyloxy)-l-(l-phenyl-lH- [1, 2,3]triazol-4-ylm ethyl)- l-azonia-bicyclo[2.2.2]octane chloridea) 4-Chloromethyl- 1 -phenyl- lH-[ 1 ,2,3]triazole (1 -Phenyl- IH-[1, 2, 3]triazol-4-yl)-methanol (700 mg) was treated with thionyl chloride (2 mL) in dichloromethane (10 mL). The mixture was stirred and heated under reflux to form a solution. The excess reagent and solvent were removed and the residue dissolved in dichloromethane (50 mL) and passed down a plug of silica gel. The silica was washed with dichloromethane followed by ether and the eluants combined and concentrated to afford the sub-titled compound as a crystalline solid (600 mg).1H NMR (399.826 MHz, CDCl3) delta 8.00 (s, IH), 7.73 – 7.68 (m, 2H), 7.54 – 7.48 (m, 2H), 7.47 – 7.41 (m, IH), 4.77 (s, 2H).

The synthetic route of 103755-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ARGENTA DISCOVERY Ltd.; FORD, Rhonan; WO2009/139709; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 13423-60-4, A common heterocyclic compound, 13423-60-4, name is 1-Phenyl-1H-1,2,4-triazole, molecular formula is C8H7N3, 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 113 1-phenyl-4-(hepr-1-yl)triazolium bromide 0.150 g (0.002 mol) 1-phenyltriazole 1 (actually, 0.3 g, there were still 2 eq. DMF contained in the educt) and 0.97 ml (1.110 g, 0.006 mol) 1-bromoheptane 2 are combined in a pressure tube. The reaction mixture was stirred 12 h at 110 C. The reaction mixture is cooled down and the same volume petroleum ether is added. The precipitated solid is filtered off, washed with petroleum ether, and dried in HV. M 324.26 C15H22N3Br Yield: 0.225 g (69%) 1H-NMR DM-170 (300 MHz/DMSO): delta (ppm)=0.87 (t, 3H, 13-H); 1.30 (m, 8H, 9/10/11/12H); 1.95 (qui, 21-1,8-H); 4.34 (t, 2H, 7-H); 7.68 (m, 3H, 5/5’/6H); 7.95 (d, 2H, 4/4′-H); 9.55 (s, 1H, 1-H); 11.10 (s, 1H, 2-H) 13C-NMR DM-170 (300 MHz/DMSO):

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; TECHNISCHE UNIVERSITAET DRESDEN; US2011/105761; (2011); 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 7343-34-2 as follows. category: Triazoles

In a 50 mL round-bottomed flask under N2 at 0 ¡ãC, sodium hydride (60percent in mineral oil, 0.184 g, 4.60 mmol) was added to a solution of 3,5-dimethyl-lH-l,2,4-triazole (0.311 g, 3.20 mmol) in DMF (12 mL) and the mixture was stirred for 20 min. 4-Bromobenzyl bromide (0.960 g, 3.84 mmol) was then added to the mixture and stirring was continued at RT for 2.5 h. The reaction mixture was then poured into H20 and the product was extracted with EtOAc (x3). The combined organic extract was washed with 0 (x3) and brine, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified on ISCO using a 40 g column (0-20percent MeOH-DCM) to afford the title compound (0.382 g, 1.44 mmol, 45percent yield) as an off-white solid. LC (Method B): 1.538 min. MS (APCI): calcd for C11H13BrN3 [M + H]+ m/z 266.0, found 266.1. 1H NMR (400 MHz, CDCI3) delta ppm 7.43 – 7.52 (m, 2H), 7.00 – 7.08 (m, J = 8.22 Hz, 2H), 5.16 (s, 2H), 2.37 (s, 3H), 2.35 (s, 3H).

According to the analysis of related databases, 7343-34-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 41253-21-8, A common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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.

(ii) Preparation of crude anastrozole of formula-I; Into a 10L, three-necked RB flask was charged l.4kg of above crude compound of formula-V and 7L of anhydrous DMF. The reaction mass was stirred for 30min and added 0.65kg of solid sodium triazole (prepared by reaction of molar quantities of 1,2,4- IH-triazole and sodium hydroxide in isopropanol at reflux temperature and isolated by filtering of the reaction mass at room temperature) in lots keeping the temperature below 25 C. The reaction mass was maintained under stirring at this temperature for 4hr. HPLC of the reaction mass indicated the absence of starting material. The reaction mass was transferred into a 50L flask containing 21L of water and stirred for 30min. Reaction mass was extracted with toluene (2 x 3L and 1 x 1L). Toluene layers were combined and . washed with water (2 x 2L). Toluene was distilled of from the filtrate under vaccum to get 1.2kg of crude anastrozole.; Example 3; Preparation of pure anastrozole of the formula-I; (i) Preparation of crude anastrozole; Into a 1L, three-necked RB flask was charged 45g of anhydrous sodium triazole and 250ml of dry DMF under nitrogen atmosphere. The reaction mass was cooled to 25 C. Bromo compound of formula-V (100g, prepared according to the process given in EP 0296749, example 1) was added to the reaction mass over a period of 2hr. The reaction mass was maintained at this temperature until the completion of reaction. The reaction mass was transferred into 3L flask containing 1.6L of water and stirred for 30min. Reaction mass was extracted with toluene (2 x 300ml and 1 x 100ml). Toluene layers were combined and washed with water (2 x 200ml). Toluene layer was treated with activated carbon (5g) and filtered. Toluene was distilled of from the filtrate under vaccum to get 95g of crude anastrozole.; Example 4; Preparation of pure anastrozole of the formula-I; (i) Preparation of crude anastrozole; Into a 1L, three-necked RB flask was charged 60g of sodium triazole monohydrate and 400ml of dry DMF under nitrogen atmosphere. The reaction mass was cooled to 25 C. Bromo compound of formula-V (100g, prepared according to the process given in EP 0296749, example 1) was added to the reaction mass over a period of 2hr. The reaction mass was maintained at this temperature until the completion of reaction. The reaction mass was transferred into 3L flask containing 1.6L of water and stirred for 30min. Reaction mass was extracted with toluene (2 x 300ml and 1 x 100ml). Toluene layers were combined and washed with water (2 x 200ml). Toluene layer was treated with activated carbon (5g) and filtered. Toluene was distilled of from the filtrate under vaccum to get 96g of crude anastrozole.

The synthetic route of 41253-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NATCO PHARMA LIMITED; PULLA REDDY, Muddasani; VENKAIAH CHOWDARY, Nannapaneni; WO2005/105762; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 7411-23-6, A common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, 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.

3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) and salicylic alcohol2c (447 mg, 2.9 mmol) were refluxed for 2 h in DMF (10 mL). Aftercompletion of the reaction, the mixture was cooled and poured intoH2O (30 mL). The precipitate formed was collected by filtration,washed with H2O, dried, and recrystallized from EtOH; yield: 585 mg(60%); colorless crystals; mp 149-150 C.IR (KBr): 3500-3000 (O-H), 1612, 1593, 1553, 1520, 1485, 1468,1433, 1364, 1290, 1267, 1231, 1184, 1069, 1005, 916, 837, 777, 760,721, 704 cm-1.1H NMR (400 MHz, DMSO-d6): delta = 9.09 (s, 1 H, OH), 6.91 (dd, J = 8.2,1.2 Hz, 1 H, Ar), 6.73 (t, J = 7.9 Hz, 1 H, Ar), 6.57 (d, J = 7.6 Hz, 1 H, Ar),5.26 (s, 2 H, CH2), 3.75 (s, 6 H, 2 ¡Á CH3O).1H NMR (400 MHz, CD3CN): delta = 6.91 (dd, J = 8.0, 1.4 Hz, 1 H, Ar), 6.89(br s, 1 H, OH), 6.79 (t, J = 8.0 Hz, 1 H, Ar), 6.66 (dd, J = 7.8, 1.4 Hz, 1 H,Ar), 5.27 (s, 2 H, CH2), 3.82 (s, 6 H, 2 ¡Á CH3O).13C NMR (100 MHz, DMSO-d6): delta = 148.0 (C), 144.8 (C), 139.6 (C),131.7 (C), 121.5 (C, CH), 119.5 (CH), 112.4 (CH), 56.4 (2 ¡Á CH3), 49.2(CH2).13C NMR (100 MHz, CD3CN): delta = 147.2 (C), 144.2 (C), 139.4 (C), 130.5(C), 121.4 (CH), 120.3 (C), 119.7 (CH), 111.7 (CH), 55.9 (2 ¡Á CH3), 48.7(CH2).Anal. Calcd for C10H9Br2N3O2: C, 33.09; H, 2.50; N, 11.58. Found: C,32.95; H, 2.41; N, 11.45.

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; 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

Electric Literature of 16681-65-5, The chemical industry reduces the impact on the environment during synthesis 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, I believe this compound will play a more active role in future production and life.

A solution of 1-methyl-1H-1,2,3-triazole (0.28 g, 3.37 mmol) in dry THF (3 mL) was cooled in a -78 C. bath and n-butyllithium (2.5 M in hexanes, 1.26 mL, 3.15 mmol) was added dropwise over a 20 minute period. The suspension was stirred in the cold bath for 30 minutes and then 1-acetyl-N-methoxy-N-methylpiperidine-4-carboxamide (0.74 g, 3.45 mmol, Intermediate 52: step a) dissolved in THF (3 mL) was added dropwise. The resulting suspension was stirred at -78 C. for 5 minutes then warmed to 0 C. and stirred for an additional 30 minutes. The mixture was warmed to room temperature and stirred for 2.5 hours then quenched with saturated aqueous NH4Cl. The aqueous mixture was extracted with EtOAc (2*). The combined EtOAc extracts were dried over Na2SO4, filtered, concentrated to dryness and chromatographed (EtOAc/DCM) to provide the title compound.

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

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-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. name: 3-Methyl-1H-1,2,4-triazole

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]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7170-01-6, its application will become more common.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171312; (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. Recommanded Product: 138624-97-2

To a screw cap vial 6-amino-4-methyl-2-(trifluoromethyl)-7,8-dihydro-4H-pyrazolo[1,5-a][1,3]diazepin-5(6H)-one (74mg, 0.298 mmol), l-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (158 mg, 0.417 mmol), 1-benzyl-1H-1,2,4-triazole-3-carboxylic acid (76mg, 0.358 mmol) was added and dissolved in N,N-dimethylformamide (5 mL). To the reaction mixture was added trimethyl amine (0.166 mL, 1.19 mmol), the vial was capped and stirred at RT for 16 h. The mixture was concentrated to dryness in vacuo and the residue was purified by RP-HPLC affording 1-benzyl-N-(4-methyl-5-oxo-2-(trifluoromethyl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,3]diazepin-6-yl)-1H-1,2,4-triazole-3-carboxamide (77mg, 59% yield): 1H NMR (400 MHz, DMSO-d6) delta 8.82 (s, 1H), 8.63 (d, J = 7.6 Hz, 1H), 7.49 – 7.19 (m, 5H), 6.93 (s, 1H), 5.49 (s, 2H), 4.51 – 4.42 (m, 1H), 4.39 – 4.27 (m, 2H), 3.27 (s, 3H), 2.72 – 2.59 (m, 1H), 2.48 – 2.42 (m, 1H). LC-MS RT = 4.34 min, m/z = 434.1 (M+H) +. LCMS (2 to 98% acetonitrile in water + 0.1% formic acid over 10 mins) retention time 4.34 min, ESI+ found [M+H] = 434.1.

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

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; HAMILTON, Gregory; STIVALA, Craig; CHEN, Huifen; ZHAO, Guiling; (1236 pag.)WO2017/4500; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics