Tag: M.W=100-200

Synthetic Route 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.

The Schiff base H2L was prepared by mixing hot solution 60 C of 4-((3-formyl-4-hydroxyphenyl)diazenyl)benzenesulfonamide (100.75, 0.33 mol) with hot solution 60 C of pyrazine-2-carbohydrazide (45.54 g, 0.33 mol) in 50 ml ethanol. The mixture was refluxed for 3 h. The formed solid product was separated by filtration, purified by crystallization from ethanol, washed several times with diethyl ether and dried in vacuum over anhydrous calcium chloride to give orange crystals, yield 85%.

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; Ammar, Reda A.A.; Alaghaz, Abdel-Nasser M.A.; Elhenawy, Ahmed A.; Journal of Molecular Structure; vol. 1067; 1; (2014); p. 94 – 103;,
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. 56423-63-3, name is 2-Bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 56423-63-3

Example 117BPreparation of Compound (142b)(142b)[00659] To a solution of compound (142a) (1.00 g, 2.27 mmol) in dioxane (30 mL) was added K2C03 (1.57 g, 11.4 mmol, 5 equiv.), Pd(PPh3)2Cl2 (30 mg, 3%) and 2-bromopyrazine (720 mg, 4.45 mmol, 2 equiv.). The mixture was degassed within an ultrasonic cleaner for 1 hr. Under argon protection, the reaction mixture was stirred at 90 C for 4 hr. The mixture was cooled to room temperature. The solvents were evaporated under reduced pressure. The residue was purified through FCC to give 460 mg of compound (142b). Characteristic analytical data: 1H NMR 8.67 (1H), 8.46 (1H), 8.32 (1H), 6.47 (1H, vinyl), 5.39 (1H), 4.54-4.62 (m, 1H, AcOCH).

According to the analysis of related databases, 56423-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; CHU, Daniel; WANG, Bing; YE, Tao; WO2012/83112; (2012); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, 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 16298-03-6, Formula: C6H7N3O2

1.5 equivalents of N-iodosuccinimide are added at room temperature to 5 g (32.7 mmol) of a methyl 3-aminopyrazine-2-carboxylate solution in 25 ml of dimethylformamide. The reaction medium is heated at 65¡ãC for 1 hour, added together with 0.5 equivalents of N-iodosuccinimide and maintained at 65¡ãC for 24 hours. After returning to room temperature, the solvent is evaporated and then the product is extracted several times with dichloromethane. The organic phases are combined, washed with 10percent sodium bisulfite solution, dried on magnesium sulfate and concentrated to yield 8 g (88percent) of methyl 3-amino-6-iodopyrazine-2-carboxylate in the form of a yellow solid. LCMS (EI, m/z): (M+1) 280 1H NMR: deltaH ppm (400 MHz, DMSO): 8.50 (1H, s, CHarom), 7.50 (2H, bs, NH2), 3.20 (3H, s, CH3)

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

Reference:
Patent; PIERRE FABRE MEDICAMENT; Kruczynski, Anna; Creancier, Laurent; Kaloun, El Bachir; Bedjeguelal, Karim; Rabot, Remi; EP2689779; (2014); 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. 74290-67-8, name is 2-Amino-5-bromo-3-methylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

Example 110 N-(3-((5-amino-6-methylpyrazin-2-yl)ethynyl)-2,4-difluorophenyl)-5-chloro-2-methoxypyridine-3-sulfonamide A mixture of 5-chloro-N-(3-ethynyl-2,4-difluorophenyl)-2-methoxypyridine-3-sulfonamide (108 mg), 2-amino-5-bromo-3-methylpyrazine (54 mg), dichlorobis(tricyclohexylphosphine)palladium(II) (11 mg), cesium carbonate (290 mg) and DMSO (2 mL) was stirred under microwave irradiation at 120 C. for 2 hr. After cooling to room temperature, the reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane) and further purified by HPLC (C18, mobile phase: water/acetonitrile (0.1% TFA-containing system)). Fractions containing the object product were collected, neutralized with a saturated aqueous sodium hydrogen carbonate solution and extracted 2 times with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was washed with ethyl acetate/IPE and dried under reduced pressure to give the title compound (63 mg). 1H NMR (300 MHz, DMSO-d6) delta 2.30 (3H, s), 3.93 (3H, s), 6.86 (2H, s), 7.10-7.23 (1H, m), 7.32 (1H, td, J=8.9, 6.0 Hz), 8.04 (1H, s), 8.06 (1H, d, J=2.5 Hz), 8.49 (1H, d, J=2.6 Hz), 10.46 (1H, s).

According to the analysis of related databases, 74290-67-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); 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. 19745-07-4, name is 2,5-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,5-Dichloropyrazine

Step C: A flask was charged with (S)-3-(lH-indazol-5-yloxy)-l-(piperidin-4- yl)pyrrolidin-2-one (0.120 g, 0.400 mmol), 2,5-dichloropyrazine (0.0655 g, 0.439 mmol), DIEA (d 0.742) (0.0696 mL, 0.400 mmol), and DMF (3 mL). The reaction was stirred at 100 ¡ãC overnight. The organic solvents were removed under reduced pressure. The residue was purified using preparative TLC with 10percent methanol in ethyl acetate to provide (S)-3-(lH- indazol-5-yloxy)-l-(l-(5-chloropyrazin-2-yl)piperidin-4-yl)pyrrolidin-2-one (0.0047 g, 0.0114 mmol, 2.85percent yield). Mass spectrum (apci) m/z = 413.2 (M+H).

According to the analysis of related databases, 19745-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; AICHER, Thomas Daniel; BENCSIK, Josef Roland; BOYD, Steven Armen; CONDROSKI, Kevin Ronald; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald Jay; PRATT, Scott Alan; SINGH, Ajay; TURNER, Timothy M.; WO2011/146335; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 6164-79-0, name is Methyl 2-pyrazinecarboxylate, 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. Application In Synthesis of Methyl 2-pyrazinecarboxylate

Procedure: ¡¤ Charged ST-601 (1 kg), NaH, 60 wt.% (579 g) and toluene (10 vol) and stirred at 15/25 C. No reaction (no gas evolution, exotherm or appearance change). (0157) ? Charged methyl propionate (64 g). No immediate reaction (no gas evolution, exotherm or appearance change) at 15/25 C. ? Charged MeOH (85 g) at 15/25 C. Immediately started to react (gas evolution, exotherm). Heated to 30/40 C. (0158) ? Charged methyl propionate (893 g) at 30/40 C over 5 h. The reaction was slower in the beginning, but became faster (more exotherm and gas evolution) after 1-2 h when -0.3 eq of methyl propionate was charged. Stirred at 30/40 C for 88 h. (0159) 64 h, 30/35 C, brown slurry, practically no gas evolution observed, IPC HPLCl: 74.4% + 14.1 % = 88.5% o/ ST-602 at 4.81 min and 5.62 min; 1.2% of ST -601 at 1.97 min; 5.8% of “Int” at 3.21 min. (0160) 72 h, 35 C, IPC HPLC2: 47.8% + 42.9%c=90 % o/ST-602; 0.9% ofST-601; 4.3% of “Int” 88 h, 38 C, IPC HPLC3: 60.3% + 32.6%=92.9% o/ST-602; 0.64% ofST-601; 1.8% of “Int” (0161) ? Reaction was cooled to 15/20 C. (0162) ? Charged AcOH (2.5 eq) over a minimum of 1 hr. Exothermic. Slightly thick, brown suspension. (0163) ? Charged 10% NaCl solution (8 vol) over a minimum of 1 h at 15/30 C. Slight exotherm. Brown, biphasic solution. Let stir at 15/30 C for a minimum of 30 min to dissolve all solids. (0164) ? The phases were separated. Both the aqueous and the organic phases were brown. (0165) ? The organic phase was washed with a 10% NaCl solution (5 vol). (0166) ? The organic phase was washed with NaHC03 (0.1 g/g SM) in 10% aq. NaCl solution (5 vol.) (0167) ? The organic phase was dried over anhydrous sodium sulfate (0.2 g/g SM) for a minimum of 2 hrs. (0168) ? Solids were filtered off and rinsed with Toluene (l x l vol) (0169) ? Concentrated to 3-4 vol at (0170) Isolated material: ST- 602 (0171) Lot No.: 2463-52-2 (0172) Appearance: light brown liquid (0173) Yield: Assumed 100% (1406 g net directly used in next step) HPLC: 94.3% of ST-602

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

Reference:
Patent; ST IP HOLDING AG; FRAMROZE, Bomi P.; (65 pag.)WO2016/207914; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference 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 9 N-(6-Chloro-pyrazin-2-yl)-4-hydroxy-2-n-propyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 2.97 g (10 mmols) of methyl 2-n-propyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 1.3 g (10 mmols) of 2-amino-6-chloro-pyrazine were reacted in 150 ml of xylene analogous to Example 1, yielding 2.05 g (52percent of theory) of N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-n-propyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide. C16 H15 ClN4 O4 S (394.86): Calc.: C–48.67percent; H–3.83percent; Cl–8.98percent; N–14.19percent; S–8.12percent. Found: C–48.91percent; H–3.79percent; Cl–8.90percent; N–14.18percent; S–8.03percent.

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

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. 41110-29-6, name is Methyl 3-methylpyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 41110-29-6

A solution of methyl 3-methylpyrazine-2-carboxylate (9.1 g, 59.8 mmol) in DCM (100 mL) was cooled to 0 C. was added urea hydrogen peroxide adduct (7.8 g, 83.0 mmol), followed by dropwise addition of trifluoroacetic acid anhydride (10.8 mL, 78.0 mmol). The resulting mixture was stirred at 0 C. for 1 h, and at RT for 18 h, during which LCMS indicated a mixture of two peaks corresponding to MS m/z=169.0 [M+H]+. The reaction was diluted with DCM and quenched with saturated Na2SO3 solution; the aqueous layer was back-extracted with DCM (2¡Á). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. ISCO purification (20-80% EtOAc/hexanes) afforded a mixture of two regioisomers, containing 3-(methoxycarbonyl)-2-methylpyrazine 1-oxide and 2-(methoxycarbonyl)-3-methylpyrazine 1-oxide (5.2 g, 30.9 mmol, 51.7% yield). The mixture of regioisomers was taken to next step without further purification. MS m/z=169.0 [M+H]+. A solution of the mixture of 3-(methoxycarbonyl)-2-methylpyrazine 1-oxide and 2-(methoxycarbonyl)-3-methylpyrazine 1-oxide (5.1 g, 15.2 mmol) in toluene (50 mL) was cooled to 0 C. and phosphorus oxychloride (2.8 mL, 30.3 mmol) was added under nitrogen followed by DMF (0.12 mL, 1.52 mmol). The reaction mixture was stirred at RT for 4 h, and heated to 65 C. for 18 h, cooled to RT, diluted with EtOAc and washed with saturated NaHCO3 solution. The aqueous layer was back-extracted with EtOAc (2¡Á). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. ISCO purification (0-50% EtOAc/hexanes) with care afforded both isomers: methyl 5-chloro-3-methylpyrazine-2-carboxylate (0.68 g) (minor product) denoted by peak 1 and methyl 6-chloro-3-methylpyrazine-2-carboxylate (1.50 g) (major product) denoted by peak 2. MS m/z=187.0 [M+H]+. Peak 1: 1H NMR (300 MHz, DMSO-d6) delta 8.73 (s, 1H), 3.91 (s, 3H), 2.71 (s, 3H). Peak 2: 1H NMR (300 MHz, DMSO-d6) delta 8.89 (s, 1H), 3.91 (s, 3H), 2.71 (s, 3H).

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; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 59303-10-5, name is 2-Chloro-5-methylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 59303-10-5

A microwave vial was charged with tert-butyl 4-((2S ,3R,4R)- I -acetyl-4-amino-2,3-dimethyl- 1,2,3,4-tetrahydroquinolin-6-yl)piperazine- I -carboxylate (for a preparation see Intermediate 213, 69 mg,0.151 mmol) in 1,4-dioxane (2 mL) followed by 2-chloro-5-methylpyrazine (37 mg, 0.288 mmol),then sodium tert-butoxide (27 mg, 0.281 mmol), DavePhos (12 mg, 0.030 mmol), and Pd2(dba)3 (26 mg, 0.028 mmol). The reaction mixture was heated to 100 C for 45 mm using a microwave reactor, then diluted with EtOAc and filtered through a pad of celite. The celite pad was washed with EtOAc (10 mL) and the filtrate concentrated under reduced pressure. The residue was purified by MDAP(Formic). The desired fractions were combined and evaporated in vacuo to afford the desired product

The synthetic route of 59303-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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, name: (3-Chloropyrazin-2-yl)methanamine hydrochloride

To a solution of 1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxylic acid (6 g, 33 mmol) and (3-chloropyrazin-2-yl)methanamine hydrochloride (6 g, 33 mmol) in 200 mL of DCM was added TEA (9 g, 88 mmol) dropwise. The resulting mixture was stirred at room temperature for 5 mins, and then HATU (12.5 g, 33 mmol) was added to the solution in portions at 0 C. The mixture was stirred at room temperature for 2 hours. Water was added, the DCM layers was separated, and washed with brine, dried over Na2SO4. The solvent was removed and the residue was purified by column chromatography on silica gel (PE/THF = 5/1 v/v%) to afford N-((3-chloropyrazin-2- yl)methyl)-1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxamide (1.5 g, 15 %). MS-ESI (m/z): 306 (M+1) + (Acq Method: 10-80AB_2min_220&254.1cm; Rt: 0.93 min)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (3-Chloropyrazin-2-yl)methanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald, M.; LIU, Jian; LIU, Shilan; YANG, Chundao; ZHENG, Shuling; WO2014/116504; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem