Day: January 11, 2021

Application 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.

D. (2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbon)-amino]-pentanoic acid 2-morpholin-4-yl ethyl ester (R4=H; R7=-(CH2)2-morpholine) (2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid (300 mg, 726 mumol, 1.0 eq.), EDCI (770 muL, 6.0 eq.) and HOBt (590 mg, 4.4 mmol, 6.0 eq.) were dissolved in DCM (6 mL). After stirring for 2 minutes, 4-morpholineethanol (879 muL, 10.0 eq.) was added, and the resulting mixture was stirred for 3 hours at room temperature. The mixture was diluted with DCM and washed with saturated sodium bicarbonate. The organic layer was separated, dried and concentrated. The material was purified (reverse phase column: 5-60% MeCN in water with 0.05% TFA over 30 min; compound eluted between 35-45% MeCN in water) and the clean fractions were combined and lyophilized. MeCN (7.2 mL) and 4 M of HCl in dioxane (720 muL) were added to the lyophilized material. The resulting mixture was stirred at room temperature for 0.5 hour and then the solvent was removed to yield the intermediate. 1,2,3-Triazole-4-carboxylic acid (82 mg, 726 mumol, 1.0 eq.), HATU (280 mg, 720 mumol, 1.0 eq.) and DMF (5.8 mL) were combined and the resulting mixture was stirred for 5 minutes. DIPEA (505 muL, 4.0 eq.) and the intermediate were added, and the mixture was stirred for 30 minutes. The reaction was quenched with AcOH and the product was purified by preparative HPLC to yield the title compound (60 mg, 95% purity). MS m/z [M+H]+ calc’d for C28H35N5O5, 522.26. found 522.4.

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 1455-77-2, A common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, molecular formula is C2H5N5, 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 312-amino-6- [(4-fluorophenyl)methyl] -5-methyl-4H- [ 1 ,2,4] triazolo [5,1-b] pyrimidin-7- oneEthyl 2-[(4-flourophenyl)methyl]-3-methyl-3-oxo-propanoate (314 mg , 1.32 mmol was added to 3-amino-5-amino-triazole (100 mg, 1.2 mmol) followed by glacial acetic acid (2.0 mL) and the reaction was heated at 120 ¡ãC under microwave irradiation for 15 minutes The solvent was evaporated and then basified with sodium hydrogencarbonate. The formed precipitate was filtered and washed with water, dichloromethane and MeCN to give the title compound (160 mg 49percent)1H NMR (400 MHz, DMSO-d6) 2.27 (3H, s), 3.77 (2H, s), 5.95 (2H, s), 7.06 (2H, d), 7.23- 7.25 (2H, m). m/z (ES) (M+H)+ 274.

The synthetic route of 1455-77-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BENGTSSON, Boel, Ase; BLACKABY, Wesley; CUMMING, John; FAULL, Alan, Wellington; LARSSON, Joakim; NASH, Ian, Alun; OLDHAM, Keith; PAPE, Andrew; WO2011/114148; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 288-36-8, name is 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 288-36-8, Computed Properties of C2H3N3

To 2-iodo-5-methylbenzoic acid (1.5 g, 5.72 mmol), copper(I) iodide (1.090 g, 5.72 mmol) and (lR,2R)-N,N’-dimethyl-l,2-cyclohexanediamine (0.814 g, 5.72 mmol) was added DMF (10 ml) under nitrogen and then 2H-l,2,3-triazole (0.474 g, 6.87 mmol). The reaction mixture was heated at 120 C at the microwave Personal Chemistry for 15 minutes. UPLC- MS monitor showed that the reaction was complete. After cooling at room temperature water was added and the aqueous washed with EtOAc. Then the aqueous acidified to pH =1 with aqueous 1 M HC1 and extracted with EtOAc. The phases were separated on a hydrophobic frit, the combined organic solvent was removed to give the crude product (2.4 g).The crude compound was purified by silica gel chromatography (SNAP KP-Sil lOOg cartridge) eluted with 5 CV of a mobile phase prepared with DCM (959.04 ml), acetic acid (0.96 ml) and MeOH (40 ml). The evaporation of proper fractions gave a yellow oil which was triturated with toluene (4 x 50 ml) and the title compound D44 was obtained as yellow solid (540 mg).UPLC (Basic GEN QC): rt = 0.35 minutes, peak observed: 204 (M+l) Ci0H9N3O2 requires: 203.1H NMR (400 MHz, DMSO-d6) delta ppm 2.44 (s, 3 H) 7.52 (dd, 1 H) 7.59 (s, 1 H) 7.64 (d, 1 H) 8.06 (s, 2 H).

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; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89606; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 15988-11-1, A common heterocyclic compound, 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, molecular formula is C8H7N3O2, 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.

General procedure: A mixture of dimedone (1, 1 mmol), 4-phenylurazole (2, 1 mmol), aromatic aldehyde (3a-h, 1mmol) and S-LCCO nano perovskite (0.01 g) was mixed in a high-pressure Teflon reactor, which was equipped with a magnetic stirrer and an optical fiber, which was implemented to control the reaction’s temperature. The reaction mixture was irradiated by 400 W microwave at 80 oC, for the specified reaction times. TLC with n-hexan:ethylacetate eluent was used to monitor the progress of the reactions. After reaction completion and cooling, the reaction mixtures were filtered and washed with ethanol to separate the catalyst. First, 10 mL water was added to the solution. Then, EtOH/H2O (4:1) was added to crystallize the water insoluble crude products. Then the crystals were filtered to achieve pure products (4a-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:
Article; Zahedi, Najmeh; Javid, Ali; Mohammadi, Mohammad Kazem; Tavakkoli, Haman; Bulletin of the Chemical Society of Ethiopia; vol. 32; 2; (2018); p. 239 – 248;,
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. 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, A new synthetic method of this compound is introduced below., COA of Formula: C9H7N3O2

Step (vii): tert-butyl N-{4-[(4-methoxyphenyl)methoxy]-2-[2-(2H-l,2,3-triazol-2- yl)benzamido]cyclopentyl}carbamate To a solution of ieri-butyl N-{2-amino-4-[(4- methoxyphenyl)methoxy]cyclopentyl}carbamate (1.71 g, 5.08 mmol) in dry DMF (17 ml) was added 2-(2H-l,2,3-triazol-2-yl)benzoic acid (CAS number 1001401 -62-2; 1.058 g, 5.59 mmol), HATU (2.90 g, 7.62 mmol) and triethylamine (2.125 ml, 15.25 mmol). The reaction was stirred at room temperature for 72 hours. The reaction was partitioned between ethyl acetate and water, washed with brine, dried over magnesium sulfate, concentrated in vacuo and purified by column chromatography (silica, 0-100% ethyl acetate / petrol) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.37 (s, 9 H), 1.46 – 1.59 (m, 1 H), 1.58 – 1.77 (m, 1 H), 1.86 – 1.97 (m, 1 H), 2.18 – 2.37 (m, 1 H), 3.67 – 3.79 (m, 4 H), 3.83 – 4.01 (m, 2 H), 4.32 (s, 2 H), 6.85 – 6.95 (m, 2 H), 7.17 – 7.31 (m, 2 H), 7.44 – 7.54 (m, 2 H), 7.55 – 7.66 (m, 1 H), 7.76 (s, 1 H), 7.96 – 8.05 (m, 2 H)MS ES+: 508

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; 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

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