Day: October 22, 2020

A common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, 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. 61-82-5.

General procedure: 20 mg of gamma-Fe2O3Ph-PMO-NaHSO4 was added to a roundbottomflask containing an aromatic aldehyde (1 mmol), 3-amino-1,2,4-triazole 2 (1.0 mmol), b-diketones (dimedone 3, 1,3-cyclohexadione 4 or ethyl acetoacetate 5) (1.0 mmol) and stirredunder solvent-free conditions at 100 C in certain times. Meanwhile,the progress of the reactionwas indicated by TLC (n-hexane:ethyl acetate; 7:3). With completing the reaction, 3ml ethanol waspoured and the magnetic nanocomposite was separated in thepresence of a magnetic stirring bar; the reaction mixture becameclear. The crude product was recrystallized from ethanol to give thepure product. The pure products were characterized by conventionalspectroscopic methods. Physical and spectral data for theselected compounds are represented below.

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

Reference:
Article; Haghighat, Mahdieh; Shirini, Farhad; Golshekan, Mostafa; Journal of Molecular Structure; vol. 1171; (2018); p. 168 – 178;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-88-5, 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 4928-88-5 as follows.

EXAMPLE 6 A mixture of methyl 1,2,4-triazole-3-carboxylate (26.4 g, 0.21 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (60.2 g, 0.19 mole) was melted and then 0.36 g (0.01 eq.) of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 5 hours, while maintaining the temperature of the reaction mixture at 95+-5¡ã C. And then, the reaction mixture was crystallized with 300.8 me of methanol to give 58.9 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (yield: 81percent).

According to the analysis of related databases, 4928-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lee, Tai-Au; Park, Nam-Jin; Khoo, Ja-Heouk; Lee, Byung-Cheol; US2003/120064; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, 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. 7170-01-6 name is 3-Methyl-1H-1,2,4-triazole, 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.

EXAMPLE 102 [2-Chloro-4-(3-methyl-1,2,4-triazol-1-yl)-phenyl](5H,11H-pyrrolo[2,1-c]-[1,4]benzodiazepin-10-yl)-methanone To a suspension of 60% sodium hydride in oil (0.3 g) in dimethylformamide (50 ml) was added dropwise 3-methyl-1,2,4-triazole (0.45 g). After hydrogen gas evolution ceased, 2-chloro-4-fluorophenyl-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepine-10-yl)-methanone (1.70 g) was added and the reaction mixture was heated in a sand bath at 110 C. for 18 hours. The mixture was poured onto ice, diluted with brine, and extracted with dichloromethane. The combined extracts were dried over anhydrous sodium sulfate and filtered through a short column of anhydrous sodium magnesium silicate. The solution was concentrated in vacuo and the residue was triturated with diethyl ether to give 1.25 g of the title compound as colorless crystals, m.p. 191-193 C., MS m/z: 404.1 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyl-1H-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US6511974; (2003); B1;,
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 7170-01-6 as follows. 7170-01-6

Example 93: Preparation of 4-(3-Methyl-lH-l,2,4-triazol-l-yl)benzaldehyde (DI53) To a stirring solution of 4-fluorobenzaldehyde (5.0 g, 40.32 mmol) in DMF (50 mL), were added K2C03 (3.34 g, 40.32 mmol) and 3-methyl-l,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 (3x). The combined EtOAc layer was washed with water and brine then dried over Na2S04 and concentrated under reduced pressure to afforded the title compound as a white solid (4.1 g, 60%): mp 125-128C; ]H NMR (400 MHz, CDC13) delta 10.05 (s, IH), 8.76 (s, IH), 8.02 (d, 2H), 7.85 (d, 2H), 2.50 (s, 3H); ESIMS m/z 188.04 ([M+H]+).

According to the analysis of related databases, 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William C.; HUNTER, James E.; WATSON, Gerald B.; PATNY, Akshay; IYER, Pravin S.; BORUWA, Joshodeep; WO2014/100163; (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 584-13-4 as follows. 584-13-4

5-(4J-l,2,4-Triazol”4-ylamino)-4I-(beiizyIoxy)biphenyl-2-carbonitriIe (CAB06050)To a solution of 4/?-l,2,4-triazol-4-amine (2.439 g, 29.01 mmol) in DMSO (50 mL) was added KOtBu (336 g, 30.0 mmol). The mixture was stirred for 0.5 hours at room temperature before CAB06Theta48 (4.40 g, 14.51 mmol) was added and stirring was continued for 1 hour. The mixture was poured into crashed ice and neutralized with 2M BCHSO4 solution. The precipitate was filtered off and recrystallised from EtOAc/?-hexane to give CAB06050 (5.07 g, 85%) as fine colorless needles. Mp. 180-182 0C; 1H NMR (400 MHz, DMSO-rftf) delta 5.17 (s, 2H)5 6.47 (d, J = 2.4 Hz5 IH), 6.54 (dd, J = 8.6, 2.4 Hz, IH)5 7.15 (AA’BB’, 2H), 732-7.50 (m, 7H)5 7.78 (d, J= 8.6 Hz, IH), 8.86 (s, 2H), 10.28 (S5 IH); 13C NMR (100.6 MHz5 DMSO-rf*) delta 69.4, 101.2, 111.0, 1123, 115.0, 119.1, 127,8, 127.9, 128.5, 129.7, 130.2, 135.6, 136.8, 144.1, 146.0, 150.8, 158.9; LRMS (ES+): m/z 368,2 (100%, [M+H]+); HRMS (ES+) calcd for C22H18N5O [M+H]+: 368.1506, found 368.1494.

According to the analysis of related databases, 584-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STERIX LIMITED; WOO, Lok Wai Lawrence; BUBERT, Christian; WOOD, Paul Michael; PUTEY, Aurelien; PUROHIT, Atul; POTTER, Barry Victor Lloyd; WO2011/23989; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

61-82-5,Some common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, 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: 20 mg of gamma-Fe2O3Ph-PMO-NaHSO4 was added to a roundbottomflask containing an aromatic aldehyde (1 mmol), 3-amino-1,2,4-triazole 2 (1.0 mmol), b-diketones (dimedone 3, 1,3-cyclohexadione 4 or ethyl acetoacetate 5) (1.0 mmol) and stirredunder solvent-free conditions at 100 C in certain times. Meanwhile,the progress of the reactionwas indicated by TLC (n-hexane:ethyl acetate; 7:3). With completing the reaction, 3ml ethanol waspoured and the magnetic nanocomposite was separated in thepresence of a magnetic stirring bar; the reaction mixture becameclear. The crude product was recrystallized from ethanol to give thepure product. The pure products were characterized by conventionalspectroscopic methods. Physical and spectral data for theselected compounds are represented below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61-82-5, its application will become more common.

Reference:
Article; Haghighat, Mahdieh; Shirini, Farhad; Golshekan, Mostafa; Journal of Molecular Structure; vol. 1171; (2018); p. 168 – 178;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, 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 6523-49-5. 6523-49-5

General procedure: An aqueous solution of cesium carbonate (130 mg, 0.4 mmol) in water (300 ul) was dispensed into each well containing a pre-mixed solution of 4-chloro-N-(4-methoxyphenyl)pyridin-2-amine (58.8 mg, 0.2mmol), respective aniline (0.26 mmol), xantphos (13.9 mg, 0.024mmol) and palladium (II) acetate (3.6 mg, 0.016 mmol) in DMA (1.25 ml). The resultant plate was placed on a pre-heated SOPHAS base plate set at 150 oC and shaken for 1 hour. The plate was cooled to room temperature and MP-TMT resin (90 mg) added to each well prior to shaking overnight at room temperature. The following day each well was transferred to a 48 well filter plate, washing through with an extra aliquot of DMA (200 ul) before a final centrifuge. The crude filtrates were then purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5mu silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford required N2-(4-methoxyphenyl)-N4-[aryl]pyridine-2,4-diamine (23-42%) N2-(4-methoxyphenyl)-N4-[4-(1,2,4-triazol-1-yl)phenyl]pyridine-2,4-diamine (5a) 28%, LCMS (tR = 2.49 min., purity = 100%), ESI+ m/z, 359.08 (M+H)+; 1H NMR (DMSO-d6, 500 MHz): delta 9.20 (1H, s); 8.72 (1H, s), 8.50 (1H, s), 8.20 (1H, s), 7.85 (1H, m), 7.78 (2H, m), 7.49 (2H, m), 7.32 (2H, m), 6.85 (2H, m), 6.45 (1H, s), 6.35 (1H, m), 3.72 (3H, s); 13C NMR (176 MHz, DMSO-d6) delta 157.53, 153.44, 152.03, 150.31, 147.99, 141.77, 140.89, 135.27, 130.70, 120.65, 120.15, 120.01, 113.79, 103.08, 92.70, 55.11; HRMS m/z (ESI+) calculated for C20H18ON6, 359.16149; found: 359.16107.

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 4-(1,2,4-Triazol-1-yl)aniline.

Reference:
Article; Burton, Rebecca J.; Crowther, Mandy L.; Fazakerley, Neal M.; Fillery, Shaun M.; Hayter, Barry M.; Kettle, Jason G.; McMillan, Caroline A.; Perkins, Paula; Robins, Peter; Smith, Peter M.; Williams, Emma J.; Wrigley, Gail L.; Tetrahedron Letters; vol. 54; 50; (2013); p. 6900 – 6904;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

252742-72-6, Adding a certain compound to certain chemical reactions, such as: 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, 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 252742-72-6.

Example 405 5-(4-(2-Fluorophenoxymethyl)piperidino]methyl-2,4-dihydro-[1,2,4]triazol-3-one After adding 150 mg of 5-chloromethyl-2,4-dihydro-[1,2,4]triazol-3-one, 331 mg of 4-(2-fluorophenoxymethyl)piperidine hydrochloride and 180 mg of anhydrous potassium carbonate to acetonitrile, the mixture was stirred overnight at room temperature. Water and ethyl acetate were added to the reaction mixture and the insoluble portion was filtered out to obtain the title compound (70 mg, 21percent yield). 1H-NMR (400 MHz, DMSO-d6); delta (ppm) 1.26-1.38 (2H, m), 1.67-1.80 (3H, m), 1.95-2.04 (2H, m), 2.77-2.84 (2H, m), 3.24 (2H, s), 3.88 (2H, d, J=5.6 Hz), 6.87-6.94 (1H, m), 7.06-7.21 (3H, m), 11.19 (1H, s), 11.27 (1H, br s).

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-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ozaki, Fumihiro; Ono, Mutsuko; Kawano, Koki; Norimine, Yoshihiko; Onogi, Tatsuhiro; Yoshinaga, Takashi; Kobayashi, Kiyoaki; Suzuki, Hiroyuki; Minami, Hiroe; Sawada, Kohei; US2004/167224; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-65-5, name is 1-Methyl-1H-1,2,3-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 16681-65-5, 16681-65-5

To a flask containing 1-methyl-1H-1,2,3-triazole (250 mg, 3.01 mmol) was added THF (20 mL) and the solution was cooled to -45 C. using a CH3CN-CO2 bath. n-BuLi (2.5 M in hexanes, 1.2 mL, 3 mmol) was added dropwise which produced an opaque suspension. The suspension was stirred at -45 C. for 20 minutes, then a homogeneous solution of (4-chloro-3-isobutyl-2-methoxyquinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone (848 mg, 2.21 mmol, Intermediate 66: step d) in 3 mL THF was introduced at -45 C. After 10 minutes, the reaction vessel was placed in an ice-water bath. The reaction mixture was quenched after 40 minutes with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (4*30 mL) and EtOAc:THF (1:1, 30 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (100% DCM increasing to 5% MeOH-DCM) provided the title compound as an off white amorphous solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.07 (d, J=2.2 Hz, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.32 (dd, J=8.7, 2.2 Hz, 1H), 6.99-6.88 (m, 3H), 4.24 (s, 1H), 4.09 (s, 3H), 3.92 (s, 3H), 2.80 (d, J=7.3 Hz, 2H), 2.53 (s, 3H), 2.36 (s, 3H), 2.08 (hept, J=6.8 Hz, 1H), 0.95 (dd, J=6.7, 1.5 Hz, 6H). MS (ESI): mass calcd. for C25H28ClN5O2, 465.2. m/z found 466.0 [M+H]+. The racemate was separated by chiral chromatography using: Chiralpack OD-H column, 80% heptane/20% ethanol, to give Example 133b as the first compound eluted from the chiral column and Example 133c as the second compound eluted from the chiral column.

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; JOHNSON & JOHNSON; 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.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 7343-33-1 name is 5-Bromo-1H-1,2,4-triazole, 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. 7343-33-1

A dry round bottom flask was charged with 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol), and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 mL) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100¡ã C. for 36 h. The reaction mixture was cooled to room temperature, diluted with EtOAc, filtered through a plug of Celite? and further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash chromatography (silica/EtOAc/Hexanes) yielded 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole as an off white solid (3.78 g, 73percent yield): mp 67-69¡ã C.; 1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H), 7.70 (m, 2H), 7.38 (m, 2H); 19F NMR (376 MHz, CDCl3) delta -58.02.

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

Reference:
Patent; Dow AgroSciences LLC; DENT, III, William Hunter; GIAMPIETRO, Natalie C.; US2014/275564; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics