Tag: M.W=100-200

Synthetic Route of 27398-39-6,Some common heterocyclic compound, 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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 suspension of sodium hydride (278 mg, 6.95 mmol, 60percent in oil) in DMF (10 mL) was added 1H-pyrazole (279 mg, 4.11 mmol) at RT and the resulting mixture stirred at RT for 0.5 h. 3-Chloropyrazine-2-carboxylic acid (500 mg, 3.16 mmol) was added and the mixture heated to 60°C for 2 h. After cooling to RT, water (20 mL) was added and the mixture extracted with 4.7percent MeOH in DCM (20 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated in vacuo to give the title compound as a solid. LRMS m/z (M+H) 191.0 found, 191.0 required.

The synthetic route of 27398-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Douglas; LUO, Yunfu; MENG, Na; YU, Tingting; (114 pag.)WO2016/65585; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

In a 100 mL three-necked flask, under N2 protection,Add magnesium chips (0.729g, 30mmol),Add 1 iodine (initiator),Add 10 mL of dry THF to immerse the magnesium chips,Start stirring,Add 2,3-dichloropyrazine (0.148 g, 1 mmol),Heating causes the reaction,THF reflux,The color of the iodine particles fades,Magnesium turnings indicate brightening,Lead to success.Stop heating,A solution of 2,3-dichloropyrazine in THF (4.291 g, 29 mmol, dissolved in 20 mL of dry THF) was slowly added dropwise.After the drop is over,Heated back to 65 degrees CelsiusFlow 1h.Get a new format reagent,The concentration is about 1 mol/L.At 100mLIn an eggplant-shaped bottle,JoinTetrabutylammonium chloride (0.278 g, 1 mmol),Under N2 protection,Slowly add the previously prepared format reagent (15mL, 15mmol).Stir at room temperature for 10 min,Then add diethylene glycol dimethyl ether (2.012g,15mmol),After stirring for 30 min at room temperature,Cool down to 0 to 5 degrees Celsius,A solution of 4-methylimino-N-2-pyridine-benzamide in THF (2.251 g, 10 mmol, 1.0 M in THF) was slowly added.After the addition was completed, the reaction solution was gradually warmed to room temperature for 2 h.After completion of the reaction, the reaction was quenched with 5 mL of aqueous hydrogen chloride (10%).Add 150 mL of a saturated aqueous solution of sodium bicarbonate,Extract twice with 100 mL of ethyl acetate.The organic layers were combined and washed with a saturated aqueous solution of sodium chloride.Dry over anhydrous sodium sulfate for 1 h,Dry under reduced pressure to obtain a crude product.Column chromatography with ethyl acetate/petroleum ether (1:2) gave 4-[amino-(3-chloro-2-pyridin2.82 g of pyrazinylmethyl]-N-(2-pyridyl)benzamide,The yield was 85% and the purity was 98%.

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; Anqing Qichuang Pharmaceutical Co., Ltd.; Wu Xueping; Chu Yijie; Chen Yao; Wang Min; (10 pag.)CN109020977; (2018); A;,
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. 123-32-0, name is 2,5-Dimethylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2,5-Dimethylpyrazine

To a solution of 2,5-dimethylpyrazine (500 mg, 4.62 mmol) in carbon tetrachloride (7 mL) was added NCS (679 mg, 5.09 mmol) followed by BPO (20 mg) and the mixture was heated to 80 C. for 6 hours. The mixture was diluted with DCM and extracted with saturated aqueous sodium sulfite solution and brine. The organic layer was dried and concentrated to give a crude product which was purified via silica gel chromatography eluting with petroleum ether/ethyl acetate (1:0 to 15:1) to give 2-(chloromethyl)-5-methylpyrazine (133 mg, 20.19% yield) as yellow oil. LCMS retention time 0.557 min; LCMS MH+ 143.

According to the analysis of related databases, 123-32-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HYDRA BIOSCIENCES, INC.; Chenard, Bertrand L.; Gallaschun, Randall J.; Kimball, Spencer David; US2014/275528; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 22047-25-2, These common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, 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.

2-Acetylpyrazine (1.22 g, 0.01 mol) and isoniazid (1.37 g, 0.01 mol) were dissolved in 20 mLabsolute ethanol, and 2 drops formic acid was added as a catalyst. The mixture was refluxedfor 5 h, and the white precipitate formed was isolated by filtration to give HL (2.17 g, 90%). IR (KBr, cm-1): 3559, 3030, 1662, 1632, 1562, 1473, 1437, 1420, 1355, 1294, 1153, 1130, 1070,1026, 997, 825, 788, 723, 624, 523, 483. 1H NMR (500 Hz, CDCl3, delta): 9.21 (s, 1H), 9.00 (s, 1H),8.81 (d, J = 10 Hz, 2H), 8.53 (d, J = 10 Hz, 2H), 7.73 (d, J = 5 Hz, 2H), 2.45 (s, 3H). Anal. Calcd forC12H11N5O: C, 59.92; H, 4.59; N, 29.03. Found: C, 72.21; H, 4.57; N, 29.16.

The synthetic route of 22047-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Shan-Shan; Wang, Peng; Wang, Li-Na; Fu, Lin; Han, Xiao-Meng; Qin, Jie; Qian, Shao-Song; Journal of Coordination Chemistry; vol. 70; 5; (2017); p. 885 – 897;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6705-33-5, name is Pyrazin-2-ylmethanol, 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 6705-33-5, Recommanded Product: 6705-33-5

To a stirred solution pyrazin-2-ylmethanol (500 mg, 4.545 mmol) in DCM (20 ml) was added Dess-martin periodinane (2.89 g, 6.818 mmol) and stirred for 1 hr at RT. Reaction mass was diluted with DCM (100 ml) washed with saturated sodium bicarbonate solution (50 ml X 2) twice. DCM part was separated, dried over sodium sulfate, evaporated to dryness to get 300 mg crude, which was purified by column chromatography using 100-200 silica and 20% EtOAc in hexane as eluent to afford pyrazine-2-carbaldehyde (100 mg) as brown liquid.

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

Reference:
Patent; CURADEV PHARMA PVT. LTD.; BANERJEE, Monali; MIDDYA, Sandip; SHRIVASTAVA, Ritesh; RAINA, Sushil; SURYA, Arjun; YADAV, Veejendra K; KAPOOR, Kishore Kamal; WO2014/141110; (2014); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 13924-94-2, 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. 13924-94-2, name is Methyl 5-aminopyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Production Example 33 To a solution of methyl 5-aminopyrazine-2-carboxylate (2 g) in dichloromethane (20 mL) were added pyridine (36.4 mL) and allyl chloroformate (25.2 mL) in 4 divided portions respectively, under ice-cooling, followed by stirring at room temperature overnight. To the reaction mixture was added water under ice-cooling, followed by extraction with ethyl acetate. The organic layer was sequentially washed with 1 M hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The obtained solid was collected by filtration while washing with a solvent (hexane:ethyl acetate=3:1) to obtain methyl 5-{[(allyloxy)carbonyl]amino}pyrazine-2-carboxylate (481 mg) as a white solid.

The synthetic route of Methyl 5-aminopyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; EP2236498; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, 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 36070-75-4, Recommanded Product: 5-Chloropyrazine-2-carbonitrile

General procedure: To an oven-dried round-bottom flask containing tert-butyl 2-[(R)-5-bromo-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate 3 (1.0 mmol) was added bis(pinacolato)diboron (1.1 mmol), potassium acetate (4.0 mmol) and 10 mL of anhydrous 1,4-dioxane. The resulting mixture was purged with N2 for three times. Pd(dppf)Cl2 (0.05 mmol) was added, the reaction mixture was purged with N2 again three times and heated under N2 at 110 C for 46 h. The course of the reaction was followed by TLC (5% MeOH in CH2Cl2) and LCMS. The reaction mixture was cooled to room temperature, and the aryl halide 5 (1.1 mmol)], Pd(dppf)Cl2 (0.05 mmol) and 3.5 mL of 2M aqueous solution of potassium carbonate (de-oxygenated by bubbling through N2 for 15 minutes before addition) were added. The reaction mixture was purged with N2 three times and then heated under N2 for 618 h at 110 C. The course of the reaction was followed by LCMS. The reaction mixture was cooled to room temperature, and the solvent removed under reduced pressure. The residue was partitioned between EtOAc (100 mL) and 1N NaOH solution (100 mL). The organic layer was washed with brine (100 mL), dried over Na2SO4 and the solvent was removed under reduced pressure to afford the crude product as a dark brown oil. The crude product was purified by silica gel chromatography, eluting with 010% MeOH in CH2Cl2 to afford the desired product.

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, 5-Chloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fernando, Dilinie P.; Jiao, Wenhua; Polivkova, Jana; Xiao, Jun; Coffey, Steven B.; Rose, Colin; Londregan, Allyn; Saenz, James; Beveridge, Ramsay; Zhang, Yingxin; Storer, Gregory E.; Vrieze, Derek; Erasga, Noe; Jones, Ryan; Khot, Vishal; Cameron, Kimberly O.; McClure, Kim F.; Bhattacharya, Samit K.; Orr, Suvi T. M.; Tetrahedron Letters; vol. 53; 47; (2012); p. 6351 – 6354,4;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4858-85-9, 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. 4858-85-9, name is 2,3-Dichloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

2,3-Dichloropyrazine 5 (5.0 g, 33.6 mmol) in 28% aqueousammonia solution (20 mL) in a reactor Parrwas stirred at 100 C for17 h. After cooling, the resulting mixture was filtered, the solid waswashed with water and dried in vacuo to afford compound 6 (3.0 g,70%) as a white powder. Rf 0.37 (cyHex/EtOAc 1:1); Mp: 170 C (lit.[43]: 169.4e170.1 C); 1H NMR (400 MHz, DMSO-d6): d 6.83 (bs, 2H,NH2), 7.60 (d,1H, J 2.4 Hz, H5), 7.98 (d, 1H, J 2.4 Hz, H6); 13C NMR(100 MHz, DMSO-d6): d 130.6 (CH), 132.6 (C), 141.4 (CH), 152.7 (C);MS (ESI) m/z (%): 129.8 (100) [MH], 131.8 (40). [MH2].

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, 2,3-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Marchand, Pascal; Bazin, Marc-Antoine; Pagniez, Fabrice; Riviere, Guillaume; Bodero, Lizeth; Marhadour, Sophie; Nourrisson, Marie-Renee; Picot, Carine; Ruchaud, Sandrine; Bach, Stephane; Baratte, Blandine; Sauvain, Michel; Pareja, Denis Castillo; Vaisberg, Abraham J.; Le Pape, Patrice; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 381 – 395;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-25-1, The chemical industry reduces the impact on the environment during synthesis 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

Intermediate 57A mixture of methyl 5-chloropyrazine-2-carboxylate (0.75 g), K2CO3 (1 .8 g) and 1 H- 1 ,2,4-triazole (1 .2 g) in N,N-dimethylformamide (6 mL) is heated to 100 C overnight. Analysis of the crude mixture by LCMS shows saponified product. The product is acidified with 1 N HCI and the precipitate is filtered and washed with water and diethyl ether to afford the title compound. LC (method 20): tR = 1 .06 min; Mass spectrum (APCI): m/z = 192 [M+H]+.

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, Methyl 5-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/168315; (2012); 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. 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H5ClN4

It was stirred for 4 hours at reflux mixture of the compound obtained in Step 1 (8 g) and triethyl orthoformate (32 mL). The reaction solution was cooled to room temperature, the precipitated solid was washed after filtration, with ethanol, To give the title compound followed by drying under reduced pressure (8.10g, 95%).

According to the analysis of related databases, 63286-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAIHO PHARMACEUTICAL COMPANY LIMITED; MINAMIGUCHI, KAZUHISA; OKAJIMA, SHIGEO; AOKI, SHINICHI; ASAI, MASANORI; ASAI, TAKAHIRO; YAMANAKA, HIROYOSHI; DOHI, SUGURU; (149 pag.)JP5851663; (2016); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem