Tag: M.W=100-200

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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C6H7N3O2

Bromine (3.91 g, 24.46 mmol) was added dropwise to a stirred mixture of 3- aminopyrazine-2-carboxylic acid methyl ester (1.27 g, 8.29 mmol) and hydrobromic acid (4.70 mL, 41.5 mmol) at 00C. A solution of sodium nitrite (1.44 g, 20.9 mmol) in water (6 mL) was then added dropwise. The reaction mixture was stirred for 15 min, brought to pH 8 with NaHCO3 (saturated, aqueous), and extracted with ethyl acetate (80 mL) and chloroform (50 mL). The combined organics were dried over MgSO4 and concentrated in vacuoto give 1.13 g (63%) of an orange oil which solidified on standing.

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; BAYER PHARMACEUTICALS CORPORATION; WO2006/91506; (2006); A2;,
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. 33332-28-4, name is 2-Amino-6-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H4ClN3

(d) N-(6-Chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide This compound was prepared from 4-hydroxy-2-methyl-N-cyclohexyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide, 2-amino-6-chloro-pyrazine and p-toluenesulfonic acid analogous to Example 14. Yield: 68percent of theory. Melting point: 278¡ã-279¡ã C. (decomposition). C14 H11 ClN4 O4 S (366.79). Calc.: C–45.84percent; H–3.03percent; Cl–9.67percent; N–15.28percent; S–8.74percent. Found: C–45.68percent; H–3.04percent; Cl–9.69percent; N–15.12percent; S–8.60percent.

According to the analysis of related databases, 33332-28-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4533664; (1985); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 457099-42-2, A common heterocyclic compound, 457099-42-2, name is 5-Ethynylpyrazin-2-amine, molecular formula is C6H5N3, 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.

Step 1: 2-Amino-5-ethylpyrazine. To a stirred solution of 5-ethynyl-2-aminopyrazine (18 mg; 0.151 mmol), in ethyl acetate (500 muL) was added triethylamine (63 muL; 0.45 mmol) and Pd(OH)2 (0.01 mmol; 20% wt on carbon). The reaction was placed under a hydrogen atmosphere at 45 psi and shook for 6 hours. The reaction was filtered and concentrated under reduced pressure to yield an off white solid (84% yield).

The synthetic route of 457099-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); 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. 768-05-8, name is Pyrazinoic acid hydrazide, A new synthetic method of this compound is introduced below., Formula: C5H6N4O

A solution of (+-)-1-(2-chloro-3-(trifluoromethyl)benzyl)-6-cyclopropyl-3-methoxy-5,6-dihydropyrazin-2(1H)-one (216 mg, 0.58 mmol) and pyrazine-2-carbohydrazide (88 mg, 0.63 mmol) in 1-butanol (5.8 mL) was heated at 130 C. for 16 h. After cooling to rt, the solvent was removed in vacuo. Purification by chromatography (SiO2; hexanes-100% EtOAc) afforded the desired product as a white solid (116 mg, 45%). MS (ESI): mass calcd. for C20H16ClF3N6O, 448.1; m/z found, 449.1 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 9.69-9.58 (m, 1H), 8.70 (d, J=2.6 Hz, 1H), 8.64 (dd, J=2.5, 1.5 Hz, 1H), 7.75-7.62 (m, 2H), 7.38 (t, J=7.8 Hz, 1H), 5.49 (d, J=15.9 Hz, 1H), 5.27-5.16 (m, 1H), 4.78 (dd, J=15.6, 1.7 Hz, 1H), 4.68 (ddd, J=13.9, 4.5, 2.4 Hz, 1H), 3.16 (ddd, J=9.9, 4.5, 3.3 Hz, 1H), 1.06-0.96 (m, 1H), 0.80-0.72 (m, 1H), 0.67-0.43 (m, 2H), 0.28-0.21 (m, 1H).

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; Janssen Pharmaceutica NV; Ameriks, Michael K.; Rech, Jason C.; Savall, Brad M.; US2014/275096; (2014); 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Safety of 5-Chloropyrazine-2-carboxylic acid

To a solution of 5-chloropyrazine-2-carboxylic acid (2 g) in dichloromethane (20 mL) were added DMF (0.05 mL) and oxalyl chloride (1.3 mL), followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and azeotroped with toluene. To the residue was added dichloromethane (20 mL), followed by ice-cooling, and triethylamine (4 mL) and ethyl (2E)-amino(hydroxy)iminoacetate (2 g) were added thereto, followed by stirring at the same temperature for 15 minutes. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The solid remaining in the aqueous layer was collected by filtration and dried under reduced pressure to obtain ethyl (2E)-amino({[(5-chloropyrazin-2-yl)carbonyl]oxy}imino)acetate (1.4 g) as a colorless solid. Further, the organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain ethyl (2E)-amino({[(5-chloropyrazin-2-yl)carbonyl]oxy}imino)acetate (1.9 g) as a yellow solid.

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; Astellas Pharma Inc.; EP2511265; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 768-05-8, 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. 768-05-8, name is Pyrazinoic acid hydrazide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution of the acid hydrazide 5 (2mmol, 0.27g) in absolute ethanol (10ml), the appropriate heteroaromatic ketone or substituted pyrazolaldehyde (2mmol) was added in the presence of catalytic amount of glacial acetic acid (5 drops), the mixture was refluxed for 12-16h. The product obtained was filtered, washed with diethyl ether, dried and recrystallized from ethanol.

The chemical industry reduces the impact on the environment during synthesis Pyrazinoic acid hydrazide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Hassan, Nayera W.; Saudi, Manal N.; Abdel-Ghany, Yasser S.; Ismail, Azza; Elzahhar, Perihan A.; Sriram, Dharmarajan; Nassra, Rasha; Abdel-Aziz, Marwa M.; El-Hawash, Soad A.; Bioorganic Chemistry; vol. 96; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 313339-92-3, name is 3,5-Dichloropyrazine-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 313339-92-3, category: Pyrazines

5-Chloro-2-fluoro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide (709 mg) was added to a reaction vessel containing a magnetic stirring bar together with 3,5-dichloro-pyrazine-2-carbonitrile (300 mg), 1,1-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (Pd(dppf)2Cl2) (100 mg) and cesium carbonate (1.69 g), followed by 6 ml dioxane and 1 ml water, and the mixture heated to 100 00 under stirring. After 3 h the reaction mixture was cooled to RT and quenched with a saturated aqueous sodium bicarbonate solution (40 ml) and extracted with EtOAc (3 x 80 ml). The combined aqueous phases were dried over sodium sulfate, filtered and evaporated to afford the crude product as a brown oil. Purification by flash chromatography on silica gel using a mixture of EtOAc and heptane as the eluent afforded 5-chloro-N-[4-(6-chloro-5-cyano-pyrazin-2-yl)-phenyl]- 2-fluoro-benzenesulfonamide as a brown foam after evaporation of the solvents under reduced pressure. Yield: 160 mg (22%). MS (ES-): m/e = 421.0 (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, 3,5-Dichloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; NAZARE, Marc; HALLAND, Nis; SCHMIDT, Friedemann; WEISS, Tilo; DIETZ, Uwe; HOFMEISTER, Armin; WO2013/41502; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 23611-75-8 as follows. Formula: C6H5ClN2O2

A suspension of methyl 6-chloropyrazine-2-carboxylate (3.4 g, 19.7 mmol) in THF (100 mL) was cooled to below 10 C and treated dropwise with 3M MeMgBr (Et20, 13.13 mL, 39.4 mmol), maintaining the reaction temperature below 10 C. The reaction mixture was then allowed to warm to RT. After 1 hr, the reaction mixture was concentrated then taken up in 1M HCI (aq, 150 mL) and extracted with EtOAc (3 x 70 mL). The organic layers were combined, dried (Mg504), filteredand concentrated on to silica (4 g). The crude product was purified by chromatography on silica gel (40 g column, 20-70% EtOAc/iso-hexane) to afford 2-(6-chloropyrazin-2-yl)propan-2-ol (1 .4 g, 7.71 mmol, 39% yield) as an orange oil; Rt 1.30 mins (HPLC acidic); mlz 173 (M+H) (ES); 1H NMR (500 MHz, DMSO-d6) 6 8.87 (d, J = 0.5 Hz, 1 H), 8.67 (d, J = 0.5 Hz, 1 H), 5.61 (s, 1 H), 1.46 (s, 6H).

According to the analysis of related databases, 23611-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STEP PHARMA S.A.S.; QUDDUS, Abdul; NOVAK, Andrew; COUSIN, David; CHATZOPOULOU, Elli; BLACKHAM, Emma; JONES, Geraint; THOMAS, Jennifer; WRIGGLESWORTH, Joseph; DUFFY, Lorna; BIRCH, Louise; GEORGE, Pascal; AHMED, Saleh; (277 pag.)WO2019/106156; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-28-4, A common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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 4 N-(6-Chloro-pyrazin-2-yl)-2,7-dimethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 7.5 g (26 mmols) of methyl 2,7-dimethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 4.36 g (33 mmols) of 2-amino-6-chloro-pyrazine were reacted in 40 ml of xylene and worked up analogous to Example 2. 7.2 g (73percent of theory) of N-(6-chloro-pyrazin-2-yl)-2,7-dimethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide were obtained. IR (KBr): 1645 cm-1 (CO amide).

The synthetic route of 33332-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4533664; (1985); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6905-47-1, These common heterocyclic compound, 6905-47-1, name is 2-Amino-6-methoxypyrazine, 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 solution of (9S)-2-(2-methylpyridin-4-yl)-7,8,9,10-tetrahydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine (0.6 g, 2.253 mmol) in Tetrahydrofuran (THF) (30 mL) stirred under nitrogen at room temperature was added triethylamine (1.884 mL, 13.52 mmol) and triphosgene (0.669 g, 2.253 mmol). Then reaction mixture was stirred at room temperature for 30 minutes. 6-methoxypyrazin-2-amine (0.846 g, 6.76 mmol) was added at rt. Then the reaction mixture was stirred at 65 C. for 16 hr. The reaction mixture was cooled to room temperature and concentrated under reduced pressure and was partitioned between water (20 mL) and EtOAc (50 mL). Organic layer was separated and was dried over anhydrous Na2SO4, filtered and filtrate was evaporated to give crude as brown solid (TLC eluent: 100% EtOAc: Rf-0.3; UV active). The crude was purified by column chromatography using neutral alumina and was eluted with 50% EtOAc in Hexane to afford pure (9S)-N-(6-methoxypyrazin-2-yl)-2-(2-methylpyridin-4-yl)-8,9-dihydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine-10(7H)-carboxamide (0.220 g, 0.526 mmol, 23.34% yield) as a off-white solid, LCMS (m/z): 418.3 [M+H]+. 1H NMR (400 MHz, CDCl3): delta 13.64 (s, 1H), 9.45-8.78 (m, 1H), 8.60 (dd, J=5.3, 0.8 Hz, 1H), 7.96 (d, J=0.5 Hz, 1H), 7.80 (ddd, J=5.3, 1.7, 0.7 Hz, 1H), 7.62 (dt, J=1.8, 0.7 Hz, 1H), 7.59 (s, 1H, 7.57 (s, 1H), 7.46 (d, J=8.0 Hz, 1H), 5.04 (t, J=2.6 Hz, 1H), 3.84 (s, 3H), 3.57-3.26 (m, 3H), 3.15-2.91 (m, 1H), 2.64 (s, 3H), 2.28 (d, J=14.3 Hz, 1H), 2.12-1.85 (m, 1H), 1.43 (s, 2H)

Statistics shows that 2-Amino-6-methoxypyrazine is playing an increasingly important role. we look forward to future research findings about 6905-47-1.

Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem