Triazoles

Related Products of 4928-88-5, 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. 4928-88-5 name is Methyl 1H-1,2,4-triazole-3-carboxylate, 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 15 A mixture of methyl 1,2,4-triazole-3-carboxylate (1.27 g, 0.01 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (3.18 g, 0.01 mole) was melted and then 0.076 g of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 3 hours, while maintaining the temperature of the reaction mixture at 95+-5¡ã C. And then, the reaction mixture was crystallized with 20 ml of butanol to give 2.70 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (yield: 85percent).

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

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

584-13-4, name is 4H-1,2,4-Triazol-4-amine, 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. Safety of 4H-1,2,4-Triazol-4-amine

5-(4H-l,2,4-TriazoI-4-ylamino)-4l-methoxybiphenyl-2-carbonitrile (CAB06046) To a solution of 4No.-l ,2,4-triazol-4-amine (3.441 g, 40.928 mmol) in DMSO (40 mL) was added KOtBu (4.593 g, 40.928 mmol). The mixture was stirred for 0.5 hours at room temperature before CAB06042 (4.65 g, 20.468 mmol) was added and stirring was continued for 1 hour. The mixture was poured into crushed ice and neutralized with 2M KHSO4 solution. The precipitate was filtered off and recrystallised from acetone/Et2theta to afford CAB06046 (5.07 g, 85%) as a light yellow crystalline solid. Mp, 176-177 0C; 1H NMR (400 MHz5 OMSO-d6) delta 3.81 (s, 3H)5 6.47 (d, J = 2.4 Hz5 IH)5 6.54 (dd, J = 8.6, 2.4 Hz, IH)3 7.07 (AA5BB’, 2H)5 7.43 (AA’BB 2H), 777 (J = 8.6 Hz, IH), 8.86 (s5 2H), 10.28 (s5 IH); 13C NMR (100.6 MHz, DMSO-^) delta 55.3, 101.2, H LO, 1123, 114.2, 119,1, 129.7, 130.0, 135.6, 144.1, 146.1, 150.8, 159 8; LRMS (ES+): m/z 292.3 (100%, [IvH-H]+); HRMS (ES+) calcd for C16Hj4N5O [M+H]+: 292,1193, found 292.1180; Anal. Calcd for C16Hi3N5O: C, 65.97; H5 4.50; N5 24.04. Found C, 65.9; H5 4,56; N5 23.8.

The synthetic route of 584-13-4 has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 15294-81-2, A common heterocyclic compound, 15294-81-2, name is 4,5-Dibromo-1H-1,2,3-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.

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: 10-30percent ethyl acetate in hexane) to give 4,5-dibromo-2-methyl-2H-[l,2,3]triazole (isomer B) (625 mg, 26percent yield) and 4,5-dibromo- 1 -methyl- IH-[1, 2,3]triazole (isomer A) (825 mg, 34percent 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.

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

Electric Literature 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 50 mL round-bottomed flask equipped with a magnetic stirbar was added 1-H-l, 2. 3-triazole (0.192 g. 2.78 mmol) and DMF (10 mL) and then cooled to O0C while stirring. Then. sodium hydride (60% dispersion in mineral oil) (0.133 g. 3.33 mmol) is added to the reaction mixture and was slowly allowed to warm to ambient temperature. Then, l-iodo-4 pentyne (0.647 g, 3.33 mmol) was added dropwise. The reaction mixture was then heated to 800C and allowed to stir for 2.5 hours. Water (20 mL) was then added to the reaction mixture and then extracted with ethyl acetate (2 x 20 mL). The organic phase was dried with sodium sulfate and concentrated de vacuo followed by a purification by column chromatography (ethyl acetate/hexane) to produce l-Pent-4-ynyl-lH-[1.2.3]triazole (0.349 g. 93%) as a colorless oil. iH NMR (300 MHz, CDCb) delta 7.67 (s, IH). delta 7.59 (s. IH). delta 4.53 (t. 2H). delta 2.20 (t, 2H). delta 2.17 (m. 2H), delta 2.04 (s, IH) ppm: ?C NMR (75 MHz. CDCb) delta 133.9. 123.9. 82.2, 70.4. 48.7, 28.9. 15.7 ppm: HRMS (ESI) calcd for C7H10N3 (M-) 136.0869, found 136.0866

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTH CAROLINA STATE UNIVERSITY; MELANDER, Christian; CAVANAGH, John; RITCHIE, David, F.; ROGERS, Steven, A.; HUIGENS, III, Robert, W.; WO2010/77603; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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 16681-70-2, HPLC of Formula: C3H3N3O2

1 .92 g (50 % purity, 3.00 mmol) 8-{[2-(trifluoromethyl)phenyl]sulfonyl}-3,8- diazabicyclo[3.2.1 ]octane (Intermediate 3) were reacted in analogy to example 1 , procedure 1 .2 with 0.678 g (6 mmol, 2 eq) 1 H-1 ,2,3-triazole-5-carboxylic acid to yield after work-up and purification 792 mg (62%) of the title compound 1 H-1 ,2,3-triazol-4- yl[(8-{[2-(trifluoromethyl)phenyl]sulfonyl}-3,8-diazabicyclo[3.2.1 ]oct-3-yl]methanone. (0504) LC-MS (Method 1 ): Rt = 0.96 min; MS (ESIpos): m/z = 416 [M+H]+ (0505) 1 H-NMR (400 MHz, DMSO-d6) delta [ppm]: 1 .602 (2.82), 1 .629 (2.52), 1 .689 (12.16), 1 .980 (0.53), 2.073 (1 .54), 2.327 (1 .17), 2.669 (1.20), 2.673 (0.87), 2.934 (3.84), 2.964 (4.10), 3.379 (5.16), 4.293 (5.08), 4.355 (9.64), 4.386 (4.07), 4.519 (0.72), 7.890 (1 .47), 7.908 (5.87), 7.913 (7.23), 7.920 (16.00), 7.927 (6.81 ), 7.932 (7.53), 7.936 (7.64), 7.950 (2.37), 7.955 (1 .54), 8.018 (0.79), 8.030 (7.57), 8.037 (6.89), 8.053 (5.61 ), 8.295 (7.27), 8.31 1 (6.51 ), 8.317 (6.21 ), 15.524 (0.53).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SIEBENEICHER, Holger; STEUBER, Holger; TER LAAK, Antonius; NUBBEMEYER, Reinhard; ROTTMANN, Antje; IRLBACHER, Horst; BADER, Benjamin; PETERS, Michaele; WAGENFELD, Andrea; TEREBESI, Ildiko; (123 pag.)WO2017/202817; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 13423-60-4, 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. 13423-60-4, name is 1-Phenyl-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

(L) (0.1 mmol) and AgNO3 (0.1 mmo) were stirred in 10 mL of waterAfter half an hour of filtration, the filtrate was colorless. A week after evaporation at room temperature for a single crystal X-ray diffraction of colorless crystals. Yield:55%.

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

Reference:
Patent; Tianjin Normal University; Wang, Ying; (10 pag.)CN104610288; (2016); B;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 135242-93-2, These common heterocyclic compound, 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, 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.

To a mixture of 5-[4-(trifluoromethoxy)phenyl]-3H-oxazolo[4,5-b]pyridin-2-one (60 mg, 0.2 mmol), (1 -methyl- l,2,4-triazol-3-yl)methanol (45.83 mg, 0.41 mmol) and PPh3 (106.26 mg, 0.41 mmol) in THF (ImL) was added the DIAD (81.92 mg, 0.41 mmol), and the mixture was stirred at 20 C under N2 for 16 hours. The reaction was diluted with sat.NH4Cl (10 mL), and the mixture was extracted with EtOAc (10 mL x 2). Then the combined organic phase was washed with brine (10 mL), dried over Na2S04, filtered and concentrated to give the crude product. The crude product was purified by purified by prep-HPLC [Kromasil (150 mm x 25 mm, 5 muiotaeta) A = H20 (0.05% NH4OH) and B = CH3CN; 47-87%B over 7 minutes] to give the product (21.81 mg, 0.06 mmol, 28% yield) as a solid. 1H NMR (DMSO-c 400MHz) deltaH = 8.40 (s, 1H), 8.12 (d, 2H), 7.87 (d, 1H), 7.80 (d, 1H), 7.47 (d, 2H), 5.13 (s, 2H), 3.80 (s, 3H). LCMS Rt = 1.12 min in 2 min chromatography, MS ESI calcd. for C17H13F3N5O3 [M+H]+ 392.1, found 392.0.

The synthetic route of 135242-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, 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 16681-70-2, Formula: C3H3N3O2

[0424] To a stirred solution of (2S,4S)-4-amino-5-biphenyl-4-yl-2-(2-hydroxyethoxymethyl)pentanoic acid ethylester (17 mg, 47 flillOI) in DMF (0.3 mL), was added lH-1,2,3-triazole-4-carboxylic acid (5.3 mg, 47 f.tmol) and HATU(18mg, 47 f.tmol), followed by DIPEA(25 f.LL, 141 f.tmol). Themixture was stirred for 30 minutes, then concentrated under reduced pressure to yield crude Compound I, which was usedin the next step without purification.

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, 1H-[1,2,3]Triazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, molecular formula is C2H2BrN3, 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. Application In Synthesis of 5-Bromo-1H-1,2,4-triazole

Example 6 Preparation of 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole 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 RT, 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 column chromatography EtOAc/hexanes yielded the title compound as an off white solid (3.78 g, 73percent): 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7343-33-1, its application will become more common.

Reference:
Patent; Dow AgroSciences LLC; GIAMPIETRO, Natalie C.; CREEMER, Lawrence C.; US2014/275503; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1455-77-2, 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. 1455-77-2 name is 3,5-Diamino-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.

To a stirred solution of IH- 1 ,2,4-triazole-3,5-diamine (1.0 g, 10.1 mmol), methyl 3-oxobutanoate (1.17 g, 10.1 mmol), and 2,4-dichlorobenzaldehyde (1.35 g, 10.1 mmol) in THF (30 mL) and heptane (8 mL) was added piperidine (30 mg, 0.3 mmol) and the reaction was heated to 70 ¡ãC for 2 days. The reaction was concentrated to afford crude methyl 2-amino-7-(2,4-dichlororhohenyl)-5-methyl-4,7-dihydro-[1,2,4]- triazolo[1,5-alpha]pyrimidine-6-carboxylate as a light yellow solid. [00202] HPLC Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100percent B over 4 minutes, 1 minutes hold time, A = 90percent water, 10percent methanol, 0.1percent TFA, B = 10percent water, 90percent methanol, 0.1percent TFA, RT = 3.03 min, 97percent homogeneity index.[00203] To a stirred solution of crude methyl 2-amino-7-(2,4-dichlorophenyl)-5- methyl-4,7-dihydro-[1,2,4]-triazolo[1,5-fl]pyrimidine-6-carboxylate (10.1 mmol) in CH2Cl2 (100 mL) was added DDQ (2.75 g, 12.1 mmol). The reaction was kept at room temperature for 1 h and was quenched by satd aq NaHCO3 solution. The organic layer was washed with satd aq NaHCO3 and brine prior to drying over anhydrousMgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded methyl 2-amino-7-(2,4-dichlorophenyl)-5-methyl-[ 1,2,4]- triazolo[1,5-fir]pyrimidine-6-carboxylate (2.0 g, 56percent) as a light yellow solid. [00204] 1H NMR (400 MHz, CDCl3) delta 7.59 (d, J= 1.8 Hz, 1H), 7.43 (dd, J= 1.8, 7.9 Hz, 1H), 7.29 (d, J= 7.9 Hz, 1H), 4.72 (s, 2H), 3.64 (s, 3H), 2.77 (s, 3H). [00205] HPLC Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100percent B over 4 minutes, 1 minutes hold time, A = 90percent water, 10percent methanol, 0.1percent TFA, B = 10percent water, 90percent methanol, 0.1percent TFA, RT = 2.85 min, 100percent homogeneity index. [00206] LCMS: Anal. Calcd. for C14H11Cl2N5O2 351.03; found: 352.11 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Diamino-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/71752; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics