Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, belongs to pyrazines 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 939412-86-9, HPLC of Formula: C5H7Cl2N3

13a. Synthesis of N-((3-chloropyrazin-2-yl)methyl)-3-methyloxetane-3-carboxamideTo a stirred suspension of 2-aminomethyl-3-chloropyrazine hydrochloride (content 77%; 4.34 mmol, 0.81 g) in dichloromethane (150 ml) were added 3-methyl-3-oxetanecarboxylic acid (4.34 mmol, 0.504 g), triethylamine (9.56 mmol, 1.33 ml), 4-dimethylaminopyridine (0.434 mmol, 0.053 g) and 1-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.69 mmol, 1.67 g). After stirring for 16 hours at room temperature the suspension was filtered over decalite and the decalite was washed with dichloromethane. The combined filtrates were washed with 0.3 N hydrochloric acid (350 mL), 0.03 N hydrochloric acid (350 mL) and sodium hydrogencarbonate (aq). All aqueous layers were twice extracted with dichloromethane. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to give crude material. Solid sodium chloride was added to all aqueous layers and these were extracted five times with dichloromethane. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to give a second crop of crude material. The combined crude products were purified using chromatography (silica gel, ethyl acetate) to yield N-((3-chloropyrazin-2-yl)methyl)-3-methyloxetane- 3-carboxamide (0.58 g).H NMR (CDCl3, 400 MHz): delta 1.68 (s, 3H), 4.52 (d, J = 6 Hz, 2H), 4.76 (d, J = 5 Hz, 2H), 4.98 (d, J = 6 Hz, 2H), 7.13 (brs, 1 H), 8.35 (d, J = 2 Hz, 1 H), 8.47 (d, J = 2 Hz, 1 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; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4744-50-7

General procedure: Pyrazine-2,3-dicarboxylic anhydride (1.0 g, 6.7 mmol) was dissolved in tetrahydrofuran (40 mL)in an Erlenmeyer flask and the corresponding substituted aniline (6.7 mmol, 1 equiv.) was added in one dose. The reaction mixture was stirred for 1 hour at laboratory temperature. Water (30 mL) was added into the mixture followed by the saturated aqueous solution of NaHCO3 until pH 6 to form thecorresponding 3-(phenylcarbamoyl)pyrazine-2-carboxylic acid 1-18. Obtained crystals were filtered off and washed with water. The progress of the procedure was monitored by TLC eluted with thesystem water/butanol/acetic acid 5:4:1.

According to the analysis of related databases, 4744-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Semelkova, Lucia; Jano?cova, Petra; Fernandes, Carlos; Bouz, Ghada; Jand?Ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; Molecules; vol. 22; 9; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 109-08-0, name is 2-Methylpyrazine, belongs to pyrazines 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 109-08-0, Recommanded Product: 109-08-0

To a solution of2-methylpyrazine (272 mg, 2.9 mmol) and HMPA (520 mg, 2.9mmol) in THF (2.5 mL) was added LDA (1.6 mL, 3 mmol) at -78°C dropwise. The mixture wasallowed to stir at -78°C for 30 minutes before a solution oflnt 7-2 (600 mg, 2.45 mmol) in 2 mLof THF was added. The mixture was allowed to warm to room temperature for 3 hours before it10 was quenched with 10 mL of saturated NH4Cl solution. The resulting mixture was extractedwith EtOAc (3 x 10 mL) and the combined organic washings were dried over sodium sulfate,filtered and in vacuo. The resulting residue was purified using column chromatography (25percentEtOAc/ petroleum ether) to provide Int 7-3 (100 mg, 12percent). MS (ESI): mlz (M+Ht 339.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; COBURN, Craig, A.; MALETIC, Milana; SOLL, Richard; LI, Chunsing; LUO, Yunfu; QI, Zhiqi; WO2014/4416; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 767340-03-4, A common heterocyclic compound, 767340-03-4, name is (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine, molecular formula is C16H13F6N5O, 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.

(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]-pyrazyn-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one (10 gr, 1 equivalent) and methanol (50 ml) were added to a 250 ml hydrogenation bottle at 25 C. and the bottle was subjected to vacuum and nitrogen backflush three times. The catalyst solution was added to the hydrogenation bottle and the bottle was again subjected to vacuum and nitrogen backflush three times and then to vacuum and backflush with hydrogen gas three times. The resulting reaction mixture was maintained under hydrogen at a pressure of 5 bar and heated to 55 C. The heated mixture was stirred at 5 bar pressure, at 55 C. for 3 days to obtain Sitagliptin base in methanol solution (optical purity by HPLC 97%, purity by HPLC 63.7%).

The synthetic route of 767340-03-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Teva Pharmaceutical Industries Ltd.; US2010/249140; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19847-12-2, name is Pyrazinecarbonitrile, belongs to pyrazines 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 19847-12-2, category: Pyrazines

The synthesis of 5 was similar to that of 4, but with pzn(21.0 mg, 0.2 mmol) in place of pza. The resultant solution wasallowed to evaporate slowly in darkness at room temperature forseveral days to afford the product as block-shaped clear lightbrown crystals of 5. (Yield: 68%, based on silver). Anal. Calc. (found)for AgC11H8N3O3: C, 39.08 (38.97); H, 2.38 (2.42); N, 12.43(12.52)%. IR (KBr): m (cm1) = 3421 (s), 3294 (s), 3071 (s), 1657(s), 1549 (s), 1453 (m), 1403 (s), 1358 (s), 1256 (s), 1173 (m),1059 (m), 1021 (m), 804 (s), 740 (m), 671 (m), 625 (w), 562 (m),454 (m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Pyrazinecarbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Huang, Hua-Qi; Wang, Dan-Feng; Zhang, Ting; Huang, Rong-Bin; Journal of Molecular Structure; vol. 1086; (2015); p. 99 – 108;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 944709-42-6, A common heterocyclic compound, 944709-42-6, name is 6,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine, molecular formula is C5H2Br2N4, 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: To a solu&et of 6,S-dlbrornci- [l,2,4J So[1,5-&yrathE (0.21 0.72] rtuuol, Ark Pliant) and 5- anth4th-1Herr]-an-Z3hJrE (0.12 g, 0.7?2 numi, Astatecl irue-PrOH (S ruL) was added DEA (0377 niL, 2.16 rtutvl). The nixthrr was heated to reflux for abat 24 k The resu1iir so]u&nwas cooled to it and filtered to give 8-((b-[L24kcc[LJvrath8- yVn&-45thkv&c?-JH-bo(bJ?zn?in-2(3Scv2e (0.15 g, 55percent) as a brtwn solid: ?H NMR (DM5 0-dEl) oe 9.62 (s, 1H), S.69 (s, lH 5S9 (s, 1H), 7.61-7.67 (ii,, 2H), 723(d, frS.4 H; 1H), 2.65 Qt, 1=6.4 H; 2H 2.07-2. 15 (m, 3H 1.23 (rr 1H).

The synthetic route of 944709-42-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FRIEDMAN, Michael M.; COX, Philip; FRANK, Kristine E.; HOEMANN, Michael Z.; OSUMA, Augustine; WILSON, Noel S.; XU, Xiangdong; WO2015/157955; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloropyrazine-2-carbonitrile

Weigh 3-chloropyrazine-2-carbonitrile (1.7 g, 12.48 mmol) into a 100 mL single-neck round bottom flask,40 mL of acetonitrile was added thereto, and the solution was dissolved and clarified with stirring at room temperature.Thereafter, cesium carbonate (8.1 g, 24.96 mmol) was slowly added in portions to the system.After the addition was completed, an acetonitrile (10 mL) solution in which N-deuterated methylmethanesulfonamide (2.1 g, 18.72 mmol) was dissolved was added dropwise to the system.After the dropping was completed, the system was transferred to an oil bath at 80 C and stirred under reflux.After 30 minutes, TLC monitored the consumption of raw materials completely.The oil bath was removed, and the system was allowed to cool to room temperature, followed by suction filtration, and the filter cake was rinsed with acetonitrile (100 mL) multiple times.The filtrates were combined, and the solvent was removed by rotary evaporation to obtain a crude product, which was then separated by column chromatography.1.1 g of N- (3-cyanopyrazin-2-yl) -N-deuterated methylmethanesulfonamide was obtained as a light brown oily liquid,Yield: 42.3%.

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; Chengdu Haichuang Pharmaceutical Co., Ltd.; Du Wu; Li Yu; Wen Kun; Li Xinghai; Chen Yuanwei; (20 pag.)CN110452229; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 21279-64-1, name is 5-Chloropyrazine-2-carboxamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H4ClN3O

5-Chloropyrazinamide (1, 50 mg, 0.3173 mmol), potassiumfluoride (KF) (110.43 mg, 1.90 mmol) and tetra-n-butylammonium bromide (TBABr) (20.46mg, 0.064 mmol) were added to a 10 mL RBF and placed under vacuum for 1 hour to dry.After filling the RBF with N2, 10 mL of dry DMSO stored over molecular sieves was added tothe RBF. The reaction mixture was heated to 110 C and refluxed for 30 min under N2. Afterthe reaction was shown to be complete by TLC, the mixture was cooled to room temperature, diluted with iced water and then extracted with ethyl acetate. The organic layer was dried withMgSO4 and the solvent was evaporated by vacuum to yield crude product which was purifiedby CombiFlash chromatography using a silica column and petroleum ether and ethyl acetateas the eluent.GC-EI Mass. Calculated for C5H4FN3O (M·+) 141.11, found 141.11. Two fragments peakswere also observed: M-CONH2·+ (C4H2FN2·+), m/z = 97.07 and M-CONH+ (C4H2FN2H+),m/z = 98.08.1H NMR (400 MHz, CDCl3 and CD3OD): delta 9.00 (s, 1H), delta 8.36 (d, J = 7.8 Hz, 1H). 19FNMR (400 MHz, CDCl3 and CD3OD): delta 75.17 (d, J = 7.3 Hz). 13C NMR (500 MHz, CDCl3and CD3OD): delta 164.72 (s, 1′-C), delta 161.56 (d, J = 256.5 Hz, 5′-C), delta 142.41 (d, J = 12.8 Hz, 3′-C),delta 142.27 (d, 2′-C) delta 131.78 (d, J = 38.7 Hz, 6′-C)

The synthetic route of 21279-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Zhuo; Ordonez, Alvaro A.; Smith-Jones, Peter; Wang, Hui; Gogarty, Kayla R.; Daryaee, Fereidoon; Bambarger, Lauren E.; Chang, Yong S.; Jain, Sanjay K.; Tonge, Peter J.; PLoS ONE; vol. 12; 2; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 297172-19-1, These common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine, 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.

5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine (1.0 g, 7.71 mmol) was dissolved in absolute ethanol (50 mL) and the solution was placed under a nitrogen atmosphere. Cyclohexanecarbaldehyde (1.86 mL, 15.4 mmol) was added and the reaction mixture was stirred 2 h at room temperature. Then it was cooled in an ice-bath and sodium triacetoxyhydroborate (6.54 g, 30.9 mmol) was added portionwise. Stirring was continued at room temperature overnight, after which the reaction mixture was concentrated and partitioned between dichloromethane and water. After separation of the layers, the aqueous layer was basified to pH -14. and it was extracted with dichioromethane three times. The combined extracts were dried over sodium sulfate, filtered and concentrated. Flash chromatography (gradient of methanol in dichloromethane) gave the title compound as a light yellow solid (1 .82 g).1H NMR (ODd3) 6 7.51 (s, 1 H), 6.78 (s, 1 H), 4.05 (t, J = 5.5 Hz, 2H), 3.61 (s, 2H),2.79 (t, J = 5.5 Hz, 2H), 2.32 (d, J = 7.2 Hz, 2H), 1.85 – 1.62 (m, 5H), 1.60 – 1.46 (m, 1H), 1.32-1.10 (m, 3H), 0.98-0.82 (m, 2H).LC/MS m/z 220 [M+H].

The synthetic route of 297172-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE S.A.; DIAZ-FERNANDEZ, Jose Luis; ALMANSA-ROSALES, Carmen; NIECZYPOR, Piotr; WO2015/91795; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 54608-52-5, name is 2-Hydrazinopyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Hydrazinopyrazine

Example 3: Preparation of (4aS,5aS)-methyl l-(pyrazin-2-yl)-4,4a,5,5a-tetrahydro-l/ – cyclopropa[4,5]cyclopenta[l,2-c]pyrazole-3-carboxylate (Formula (He)). To a nitrogen-purged 50-L reactor was charged (lS,5R)-bicyclo[3.1.0]hexan-2-one (2.0 kg, 20.81 mol), dimethyl oxalate (2.84 kg, 24.05 mol, 1.2 eq.), and methanol (1.53 kg). The mixture was stirred at 20-25C and sodium methoxide solution (25 wt% in methanol, 6.49 kg, 30.04 mol, 1.44 eq.) added slowly so as to keep the temperature of the reaction mixture below 40C. The internal temperature of the reaction mixture was kept between 35-40C and the mixture monitored by HPLC for the disappearance of starting material (i.e., (lS,5R)-bicyclo[3.1.0]hexan-2-one). The reactor contents were then cooled to 30C before adding 2-hydrazinylpyrazine (2.43 kg, 22.07 mol, 1.06 eq.) to the reactor. Thereafter, 6N HC1 (6.76 L) was charged slowly to the reactor while maintaining an internal temperature of 35-40C. The mixture was then stirred at 35-40C and monitored for reaction completion by HPLC. The reaction was considered complete when the diketo methyl ester intermediate of Formula (Ilc-i) was less than 3 area % as determined by HPLC The mixture was concentrated by distillation under vacuum at a jacket temperature of 25-50C until no appreciable distillate was observed. Water (19.3 kg) was charged to the reactor and the mixture concentrated by distillation under maximum vacuum at a jacket temperature of 25-50C until no appreciable distillate was observed. Water (9.65kg) was added to the reaction mixture and the mixture stirred at 20-25C for at least 1 hour. The mixture was filtered and the filter cake washed with water (2 x 9.65 kg). The solids were placed in a vacuum oven set at 45-55C and dried to a constant weight. The yield of (4aS,5aS)-methyl l-(pyrazin-2-yl)-4,4a,5,5a-tetrahydro- l/i-cyclopropa[4,5]cyclopenta[l,2- c]pyrazole-3-carboxylate was 3.09 kg (58%); NMR (DMSO- , 400 MHz): delta 0.42-0.45 (td, J = 4.5, 7.8 Hz, 1H), 1.25- 1.30 (m, 1H), 2.28-2.34 (m, 1H), 2.71 -2.74 (m, 1H), 2.77 (d, / = 16.0 Hz, 1H), 2.90 (dd, / = 6.5, 16.4 Hz, 1H), 3.83 (s, 3H), 8.61 (dd, / = 1.5, 2.6 Hz, 1H), 8.68 (d, J = 2.5 Hz, 1H), 9.16 (d, / = 1.40 Hz, 1H); 13C NMR (DMSO- , 100 MHz) delta 16.80, 17.06, 23.50, 26.18, 51.83, 129.28, 135.15, 139.57, 142.47, 142.89, 147.07, 154.47, 161.62.

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; ARENA PHARMACEUTICALS, INC.; PAL, Biman B.; MONTALBAN, Antonio Garrido; (0 pag.)WO2016/85941; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem