Month: May 2021

Application 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.

[0752] Compound 1 (4 mg, 50 f.tmol) was dissolved inMeCN (1 mL) and dry 4N HCI in dioxane (0.5 mL). Themixture was stirred for 1 0 minutes and then concentratedunder reduced pressure to yield Compound 2, which wascarried to the next step without purification

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

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

Related Products of 41253-21-8, The chemical industry reduces the impact on the environment during synthesis 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, I believe this compound will play a more active role in future production and life.

To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in THF (20 mL), and DMF (40 mL) was added 1,2,4-triazole sodium derivative (6.3 g, 70 mmol) and the mixture was stirred at 90 C. for 3 h, filtered and concentrated. The residue was adsorbed onto Silica gel and purified by flash chromatography eluting with 0%-10%-30% EtOAc/hexanes to give intermediate 1 as colorless needles (2.46 g, 18%) and intermediate 2 was obtained as a white solid (0.7455 g, 6%). Intermediate 1 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile: 1H NMR (500 MHz, CDCl3) delta: 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13. Intermediate 2 4-(1H-1,2,4-triazol-1-yl)-2-fluorobenzonitrile: 1H NMR (500 MHz, CDCl3) delta: 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13.

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, Sodium 1,2,4-triazol-1-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/112190; (2007); A1;,
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. 81606-79-3, name is 2-(1,2,4-Triazol-1-yl)acetonitrile, A new synthetic method of this compound is introduced below., Quality Control of 2-(1,2,4-Triazol-1-yl)acetonitrile

Preparation 148 N-hydroxy-2-(1H-1,2,4-triazol-1-yl)ethanimidamide Method as for preparation 1 using 2-(1H-1,2,4-triazol-1-yl)acetonitrile (J.Org.Chem. USSR, 18; 2; 1982; 407) (2.16 g, 20 mmol) as starting material. The crystalline precipitate was filtered off and washed with cold MeOH and Et2O to afford the title compound (2.37 g)

The synthetic route of 81606-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Datta, Usa; US2002/151535; (2002); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route 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.

A mixture of 3,5-dibromo-1H-1,2,4-triazole (15.5 g, 0.068 mol) andNaHCO3 (6.8 g, 0.082 mol) in DMF (150 mL) was slowly treatedwith 1,2-dibromoethane (26.0 g, 0.137 mol). The mixture was stirredfor overnight at 55 C. Then, the reaction was quenched with water(20 mL) and extracted by EtOAc (60 mL × 2). The organic layer waswashed with brine (40 mL × 2), dried over Na2SO4 and concentrated invacuo. The residue was purified by silica gel column chromatographyto provide compound 20 as: White solid; m.p. 47-48 C; yield 15.5 g(68%); 1H NMR (400 MHz, CDCl3): delta 4.52 (t, J = 6.3 Hz, 2H), 3.72(t, J = 6.3 Hz, 2H); 13C NMR (125 MHz, CDCl3): delta 142.03, 131.66,51.96, 29.10; MS (EI) m/z: 331 (M+). HRMS (EI) m/z calcd forC4H4Br3N3(M+): 330.7955; found: 330.7960.

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; Zheng, Yazhou; Qian, Anran; Ling, Chenyu; Cao, Xufeng; Cui, Yongmei; Yang, Yushe; Journal of Chemical Research; vol. 41; 4; (2017); p. 241 – 245;,
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. 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C2H2BrN3

5-Bromo-l-(4-methoxy-benzyl)-lH-[l,2 4]triazole In a 100 mL round-bottomed flask, 3-bromo-lH-l,2,4-triazole (3 g, 20.3 mmol, Eq: 1.00), 1- (chloromethyl)-4-methoxybenzene (3.18 g, 20.3 mmol, Eq: 1) and N-ethyl-N-isopropylpropan-2- amine (5.24 g, 40.6 mmol, Eq: 2) were combined with acetonitrile (101 ml) to give a light yellow solution. Potassium iodide (1.68 g, 10.1 mmol, Eq: 0.5) was added. The mixture was heated to reflux for 2 hours. The mixture was cooled down and poured into water (50 mL) and extracted with EtOAc (3×50 mL), the combined extracts were washed with water (50 mL) and brine (50 mL), dried over anhydrous Na2S04, concentrate to afford the crude product. Purify the compound by column chromatography (hexanes/ EtOAc = 70/30) to afford the oil 1.1 g (20percent).

According to the analysis of related databases, 7343-33-1, 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.; DING, Qingjie; JIANG, Nan; WEIKERT, Robert James; WO2014/135472; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 4928-87-4, A common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-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.

To an ice-cold solution of CLB (0.21 g, 1.0 mmol) in DMF (1.2 mL), TCA (0.14 g, 1.2 mmol), iPr2NEt (0.52 mL, 3.0 mmol) and bromotripyrrolidinophosphonium hexafluorophosphate (PyBrOP) (0.67 g, 1.44 mmol) were added sequentially. The reaction mixture was stirred at ambient temperature for 2 h and then diluted with EtOAc. The organic phase was washed twice with a 5% aq solution of NaHCO3 and thrice with H2O, dried over Na2SO4 and evaporated to dryness to afford an oily residue. Conjugate 8 was purified with FCC. Yield: 0.25 g (80%); white foam; Rf (CHCl3/MeOH 8:2): 0.26; IR (KBr, cm-1): 3122, 3028, 2927, 2840, 1655, 1541, 1426, 1334, 1256, 1062, 807, 739; MS (ESI, 30 eV): m/z 637.19 [2 M+Na], 346.33 [M+K], 330.39 [M+Na], 308.41 [M+H]; HRMS (m/z): [M+H]+ calcd for C12H14N5O5, 308.0995. Found: 308.0948; 1H NMR (d6-DMSO, 40 C): delta 8.40 (s, 1H), 8.13 (d, J = 8.8 Hz, 2H), 7.68 (d, J = 9.2 Hz, 1H), 7.62 (d, J = 8.8 Hz, 2H), 7.61 (s, 1H), 7.00 and 6.99 (two s, 2H), 5.13 (d, J = 2.4 Hz, 1H), 4.22-4.15 (ddt, J = 2.4, 7.6 and 9.2 Hz, 1H), 3.66 (1H, dd, J = 7.6 and 10.8 Hz), 3.52 (1H, dd, J = 7.6 and 10.8 Hz); 13C NMR (d6-DMSO): delta 172.6, 158.1, 152.0, 146.9, 135.6, 127.6 (2C), 123.5 (2C), 69.4, 61.0, 56.7.

The synthetic route of 4928-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Magoulas, George E.; Kostopoulou, Ourania N.; Garnelis, Thomas; Athanassopoulos, Constantinos M.; Kournoutou, Georgia G.; Leotsinidis, Michael; Dinos, George P.; Papaioannou, Dionissios; Kalpaxis, Dimitrios L.; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3163 – 3174;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic 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. Quality Control of 2-(2H-1,2,3-Triazol-2-yl)benzoic acid

Step C: (2-(2H-1,2,3-triazol-2-yl)phenyl)((1S,4S,6R)-6-((5-(trifluoromethyl)pyridin-2-yl)amino)-2-azabicyclo[2.2.1]heptan-2-yl)methanone To the title compound of step B (30 mg) and intermediate A-1 (19 mg, 0.10 mmol) in DMF (1 mL) was added DIPEA (94 muL, 0.55 mmol) and HATU (38 mg, 0.10 mmol), and the reaction mixture was stirred at room temperature for 1 h. The reaction was quenched by the addition of H2O and the aqueous layer was extracted with 4:1 EtOAc/hexanes (3*). The combined organics were washed with H2O, 5% aqueous LiCl, brine, dried with Na2SO4, filtered, and concentrated. Purification via silica gel chromatography (25-100% EtOAc (with 10% MeOH) in hexanes) gave the title compound (20 mg). MS (ESI) mass calcd. C21H19F3N6O, 428.2; m/z found 429.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6, Compound presents as a mixture of rotamers, major rotamer reported) delta 8.10 (s, 2H), 7.94-7.77 (m, 1H), 7.70 (d, J=8.1 Hz, 1H), 7.67-7.49 (m, 2H), 7.28 (td, J=7.7, 1.5 Hz, 1H), 6.96-6.82 (m, 1H), 6.77-6.56 (m, 2H), 3.96 (br. s, 1H), 3.64 (br. s, 1H), 3.33-3.25 (m, 1H), 3.23-3.14 (m, 1H), 2.15-2.00 (m, 1H), 1.44-1.33 (m, 1H), 1.23-1.03 (m, 2H), *1H buried under DMSO-d6 peak.

The synthetic route of 2-(2H-1,2,3-Triazol-2-yl)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; GELIN, Christine F.; LEBOLD, Terry P.; SHIREMAN, Brock T.; US2014/275118; (2014); A1;,
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. 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Formula: C3H5N3

Into a macrowave tube, 4-methyl-1 H-1 ,2,3-triazole (473 mg, 5.69 mmol) was dissolved in THF (10 ml) and cooled to 0C, NaH (341 mg, 8.54 mmol) was added and stirred for 1 h at rt. A solution of 4-(4-methoxyphenyl)butyl methanesulfonate (490 mg, 1.897 mmol) in DMF (2.00 ml) and THF (1.0 ml) was then added and heated to 60C for 3h. The mixture was diluted with EA (20 ml) and filtered through a pad of celite. The filtrate was concentrated to dryness. The crude was purified using ISCO column (DCM to 40% EA in DCM) to give two isomers. The title compound (0.13 g), 1H NMR (400 MHz, CDCb) delta ppm 1.57 – 1.64 (m, 2 H) 1.88 – 2.02 (m, 2 H) 2.29 (s, 2 H) 2.57 (t, J=7.63 Hz, 2 H) 3.78 (s, 3 H) 4.35 (t, J=7.04 Hz, 2 H) 6.76 – 6.86 (m, 2 H) 7.06 (m, J=8.22 Hz, 2 H) 7.31 (s, 1 H) and 2-(4-(4-methoxyphenyl)butyl)-4-methyl-2H-1 ,2,3-triazole (0.18 g). 1H NMR (400 MHz, CDCb) delta ppm 1.60 – 1.68 (m, 2 H) 1.80 – 1.97 (m, 2 H) 2.26 (s, 1 H) 2.33 (s, 2 H) 2.52 – 2.66 (m, 2 H) 3.78 (s, 3 H) 4.16 – 4.36 (m, 2 H) 6.82 (m, J=8.22 Hz, 2 H) 7.05 (d, J=8.61 Hz, 2 H) 7.32 (m, 1 H)

The synthetic route of 27808-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE MONTREAL; GAREAU, Yves; GINGRAS, Stephane; CHANTIGNY, Yves; YANG, Gaoqiang; SAUVAGEAU, Guy; BACCELLI, Irene; MARINIER, Anne; (284 pag.)WO2019/84662; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 27996-86-7,Some common heterocyclic compound, 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, molecular formula is C9H7N3O, 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: The general procedure for the synthesis of the N-heterocycles using SnAP reagents was as follows. To a solution of the aminotributylstannane-SnAP reagent (0.50 mmol, 1.00 equiv.) in CH2Cl2 (2.5 ml) was added the corresponding aldehyde (0.50 mmol, 1.00 equiv.) and molecular sieve (MS) 4A (50 mg) under an inertat mosphere at r.t. The reaction mixture was stirred for two hours and filtered through a layer of Celite (0.3 cm), rinsing with CH2Cl2. The filtrate was concentrated under reduced pressure to afford the imine. Separately, anhydrous Cu(OTf)2 (0.50 mmol, 1.00 equiv.) was added to as olution of 2,6-lutidine (0.50 mmol, 1.00 equiv.) in HFIP (2.0 ml) in a dry Schlenk flask and stirred at r.t. for one hour, during which a homogeneous suspension formed. A solution of the imine (0.50 mmol, 1.00 equiv.) in dry CH2Cl2 (8.0 ml) was added in one portion and the resulting mixture was allowed to stir at r.t. for 12 hours (unoptimized reaction time). The reaction was quenched at r.t. with a mixture ofsaturated aqueous NaHCO3 (4 ml) and 10% aqueous NH4OH (2 ml). The mixturewas stirred vigorously for 15 minutes, the layers were separated and the aqueous layer was extracted with CH2Cl2 (3 × 5 ml). The combined organic layers were washed with H2O (3 ×5 ml) and brine (10 ml), dried over Na2SO4, filtered, concentrated and purified by flash column chromatography on silica gel using a precolumn of KF (3 cm).

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

Reference:
Article; Vo, Cam-Van T.; Luescher, Michael U.; Bode, Jeffrey W.; Nature Chemistry; vol. 6; 4; (2014); p. 310 – 314;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 60166-43-0, The chemical industry reduces the impact on the environment during synthesis 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole, I believe this compound will play a more active role in future production and life.

(R)-3-Bromo-7-chloro-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H- pyrrolo[2,3-b:4,5-b’]dipyridine (30.0 mg, 0.066 mmol), l,4-dimethyl-lH-l,2,3-triazole (25.5 mg, 0.263 mmol), Me4NOAc (21.8 mg, 0.164 mmol), and PdCl2(dppf)2.DCM (3.8 mg, 4.60 muetaiotaomicron) were weighed into a 20 mL scintillation vial, and 3 mL DMF was added and the air was replaced with nitrogen. The reaction mixture was heated to 100 C with stirring. After 1 h, it was cooled to room temperature, filtered, and concentrated. The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge C18, 19 x 200 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 ACN: water with 10-mM NH4OAc; Mobile Phase B: 95:5 ACN: water with 10-mM NH4OAc; Gradient: 20-60% B over 15 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 4.2 mg, and its estimated purity by LC/MS analysis was 100%. Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7-muetaiota particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAc; Temperature: 50 C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 1 mL/min; Detection: UV at 220 nm, RT = 1.52 min, LC/MS (M+H) = 534.5, LC/MS (M+H) = 534.5. Injection 2 conditions: Column: Waters BEH CI 8, 2.0 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 methanol: water with 10 mM NH4OAc; Mobile Phase B: 95:5 methanol: water with 10 mM NH4OAc; Temperature: 50 C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 0.5 mL/min; Detection: UV at 220 nm. RT = 2.50 min, LC/MS (M+H) = 534.5. NMR (500MHz, DMSO-c e) delta 8.82 (d, J=8.1 Hz, 1H), 8.67 (s, 1H), 8.58 (br. s., 1H), 7.74 (t, J=7.2 Hz, 3H), 7.36 – 7.28 (m, 2H), 7.28 – 7.20 (m, 1H), 6.07 (br. s., 1H), 4.39 (s, 3H), 4.03 (s, 3H), 3.89 (d, J=13.6 Hz, 1H), 3.75 (d, J=9.9 Hz, 1H), 3.61 (br. s., 1H), 3.43 (t, .7=11.2 Hz, 1H), 3.24 (t, .7=11.4 Hz, 1H), 2.55 (s, 3H), 2.31 (s, 3H), 1.62 (br. s., 1H), 1.51 – 1.39 (m, 1H), 1.29 (d, J=8.4 Hz, 1H), 1.15 (br. s., 1H); LC/MS (M+H) = 534.3 [Column: Waters Aquity BEH C18 2.1 X 50 mm 1.7u; Mobile Phase A: water with 0.05% TFA; Mobile Phase B: ACN with 0.05% TFA; Temperature: 40 C; Gradient: 2-98% B over 1.5 min; Flow: 0.8 rnL/min].

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, 1,4-Dimethyl-1H-1,2,3-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics