Tag: M.W=100-200

Related Products of 6705-33-5,Some common heterocyclic compound, 6705-33-5, name is Pyrazin-2-ylmethanol, molecular formula is C5H6N2O, 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 pyrazin-2-ylmethanol (55 mg, 0.5 mmol) in THF (4 mL) was added potassium tert-butoxide (110 mg, 1.0 mmol). After stirring for 10 min, Example 27G (100 mg, 0.25 mmol) was added to the reaction mixture in portions. The mixture was stirred at ambient temperature for 2 hours, quenched with saturated aqueous NH4Cl and extracted by EtOAc (3×10 mL). The combined organic extracts were concentrated under reduced pressure. Purification by flash chromatography (silica gel, MeOH/Et3N (10:1) in CH2Cl2 in 0-30% gradient) provided 61 mg (47%) of the title compound. 1H NMR (300 MHz, DMSO-d6) delta ppm 0.34-0.49 (m, 4H), 1.08-1.24 (m, 1H), 1.33-1.44 (m, 9H), 3.90 (s, 3H), 4.15 (d, J=7.1 Hz, 2H), 5.39 (s, 2H), 6.83 (s, 1H), 7.27 (d, J=8.8 Hz, 1H), 7.60 (dd, J=8.7, 1.9 Hz, 1H), 7.77 (d, J=2.4 Hz, 1H), 8.56-8.70 (m, 2H), 8.93 (d, J=1.4 Hz, 1H); MS (DCI/NH3) m/z 488 (M+H)+

The synthetic route of 6705-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; US2010/69348; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5521-58-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5521-58-4 name is 5-Methylpyrazin-2-amine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 3: 3-Methoxy-4-[3-(5-methyl-pyrazin-2-yl)-ureido]-benzoic acid methyl ester. To a stirred solution of 3-methoxy-4-(4-nitro-phenoxycarbonylamino)-benzoic acid methyl ester (11.7 g, 33.8 mmol) in 34 mL NMP at room temperature under nitrogen was added 5-methyl-2-aminopyrazine (3.69 g, 33.8 mmol) and the reaction was immersed in an 85 C. oil bath. After 6 hours the reaction was allowed to cool to room temperature and a precipitate formed. EtOAc (200 mL) was added and the precipitate was isolated by filtration (4.7 g, 44%). 1H-NMR (400 MHz, d6-DMSO) 6 8.79 (br s, 1H), 8.36 (d, 1H), 8.23 (s, 1H), 7.60 (d, 1H), 7.52 (s, 1H), 3.98 (s, 3H), 3.81 (s, 3H), 2.42 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methylpyrazin-2-amine, and friends who are interested can also refer to it.

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

Application of 36070-80-1, These common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-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.

To a suspension of 5-chloropyrazine-2-carboxylic acid (365 mg, 2.302 mmol) in anhydrous DCM (6 mL) was added oxalyl dichloride (1.381 mL, 2.76 mmol), followed by a few drops of DMF. The reaction mixture was stirred at room temperature overnight. Solvent was evaporated, the residue was dissolved in anhydrous DCM (6 mL), 3-methoxyazetidine hydrochloride (341 mg, 2.76 mmol) was added, followed by DIEA (1.404 mL, 8.06 mmol). The reaction mixture was stirred at room temperature for 5 h. Solvent was evaporated, the residue was dissolved in ethyl acetate, washed with 5% citric acid solution, saturated NaHC03 aqueous solution, brine, and dried over anhydrous Na2S04. The mixture was filtered and concentrated. The residue was purified by column chromatography with 60% ethyl acetate/hexanes to give the title compound (269 mg, 1.18 mmol, 51 % yield) as an off-white solid. Exact mass calculated for CgHioClNsOz: 227.1 , found: LCMS mlz = 228.0 [M+H]+; lU NMR (400 MHz, CDC13) delta 3.33 (s, 3H), 4.09-4.13 (m, 1H), 4.25-4.30 (m, 1H), 4.37-4.42 (m, 1H), 4.48-4.54 (m, 1H), 4.79-4.84 (m, 1H), 8.53 (d, J = 1.3 Hz, 1H), 9.10 (d, J = 1.3 Hz, 1H).

Statistics shows that 5-Chloropyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 36070-80-1.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; BUZARD, Daniel J.; LEHMANN, Juerg; NARAYANAN, Sanju; YUE, Dawei; WO2011/127051; (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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 5-chloropyrazine-2-carboxylate

Methyl 5-(chloropyrazine)-2-carboxylate (36 7) (2g, 0.0115mmol) was dissolved in 80mL of 87 DMSO. 88 Sodium azide (3g, 0.0463mmol) and 39 triphenylphosphene (4.6g, 0.1738mmol) were added and the mixture was refluxed at 120C for 4h. 20mL of 1N 89 HCl was added and the reaction was continued at 120C for 2h. The mixture was cooled and neutralized by using 90 aqueous NaHCO3 solution and 91 product was extracted in ethyl acetate, dried using Na2SO4. The ethyl acetate fraction was evaporated and washed with n-pentane to get 0.7g (yield 39.5%) yellow solid of compound 8. 1H NMR (400MHz, DMSO-d6) delta 8.53 (d, J=1.2Hz, 1H), 7.91 (d, J=1.2Hz, 1H), 7.39 (s, 2H), 3.79 (s, 3H). C6H7N3O2 [M]: 153.14; MS (ESI) m/z: [M-H]+: 152.05.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 33332-25-1.

Reference:
Article; Trivedi, Prakruti; Adhikari, Nilanjan; Amin, Sk. Abdul; Jha, Tarun; Ghosh, Balaram; European Journal of Pharmaceutical Sciences; vol. 124; (2018); p. 165 – 181;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 69214-33-1,Some common heterocyclic compound, 69214-33-1, name is 8-Chloroimidazo[1,2-a]pyrazine, molecular formula is C6H4ClN3, 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 slurry of Intermediate B (400 mg, 1.6 mmol), 8-chloroimidazo[l,2-a]pyrazine (272 mg, 1.77 mmol) and Hunig’s Base (0.84 ml, 4.8 mmol) in DMA (10 ml) was heated at 75 C overnight. The cooled reaction mixture was partitioned between ethyl acetate and sat. aqueous sodium bicarbonate solution. The organic layer was washed with brine (2 x 50 mL) followed by water (2 x 50 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated to dryness. The crude oil was dissolved in minimal DCM and purified by silica gel column chromatography (0-100% ethyl acetate in hexanes, 20 min) to afford 21-1 as an oil. LRMS m/z (M+H) 366.3 found, 366.4 required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Chloroimidazo[1,2-a]pyrazine, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; SKUDLAREK, Jason, W.; (0 pag.)WO2016/85784; (2016); 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., Computed Properties of C5H6N4O

General procedure: The 2-(3-methylbutanoyl)-1H-indene-1,3(2H)-dione neededfor the synthesis was prepared by the Claisen condensation of diethylphthlate and appropriate ketone under the inuence ofsodium methoxide according to the procedure as described inthe literature.32,33 Schi bases were synthesized by dissolving 1:1molar ratio methanolic solution of 2-(3-methylbutanoyl)-1Hindene-1,3(2H)-dione with benzoic acid, pyrazine acid, nicotinic acid, and isonicotinic acid hydrazides. The solution wasstirred and reuxed for 5-6 h. The solution was kept overnightat room temperature. The white and red color solids so obtainedwere fltered and recrystallized in methanol and chloroformsolution (1:1, v/v).

The synthetic route of 768-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khatkar, Priyanka; Asija, Sonika; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 4; (2017); p. 446 – 453;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 74290-67-8,Some common heterocyclic compound, 74290-67-8, name is 2-Amino-5-bromo-3-methylpyrazine, molecular formula is C5H6BrN3, 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 2-amino-5-bromo-3-methylpyrazine (46.5 g, 247.3 mmol) in acetonitrile (450 mL) and THF (750 mL) was added DMAP (3 g, 24.7 mmol). The reaction mixture was stirred for 15 minutes before the addition of di-tert-butyl dicarbonate (242 g, 1 112.8 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated in vacuo, then diluted with EtOAc (750 mL) and washed with water (500 mL). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The black tar was purified via flash chromatography, using a 10-15% EtOAc in heptane gradient. The resultant solid was triturated with IP A. The resulting white solid (the bis-tert-butoxycarbonyl derivative) was dissolved in methanol (3000 mL), then K2CO3 (61.25 g, 443 mmol) was added. The reaction mixture was stirred overnight at room temperature, then at 60C for 1 h, then allowed to cool and concentrated in vacuo. The residue was dissolved in DCM (1000 mL), then washed with water (2 x 1000 mL) and brine (500 mL). The organic layers were dried over magnesium sulphate, then concentrated in vacuo, to give the title compound (38 g, 80% pure by LCMS). LCMS (ES+) [M+H]+ 288.1 and 289.1 , RT 1.42 minutes (method 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-bromo-3-methylpyrazine, its application will become more common.

Reference:
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; HORSLEY, Helen Tracey; HUANG, Qiuya; REUBERSON, James Thomas; VANDERHOYDONCK, Bart; WO2014/96423; (2014); 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. 356783-16-9, name is 3,6-Dichloropyrazine-2-carbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3,6-Dichloropyrazine-2-carbonitrile

KF2H2O (1.3 g, 6 eq) and TBAB (tetrabutylammoniumbromide) (0.3 g, 0.4 eq) were added into the mixed solventcontaining 4 mL of DMSO and 8 mL of toluene. Thetoluene was subsequently removed by distillation underreduced pressure. A further 8 mL of toluene was thenadded and once again removed by distillation underreduced pressure with the purpose of removing the moisture of the reagent relating to the reaction. Then, 3,6-dichloropyrazine-2-carbonitrile (0.4 g, 1 eq) was addedand the mixture was stirred at 50 C for 3 h. Subsequently,anhydrous K2CO3 (0.04 g) and 30% H2O2(0.28 mL) were added into the solution at 0 C stirring for1.5 h at 25 C. Water (1 mL) and NaHCO3 (0.132 g)were added into the 3,6-difluoropyrazine-2-carboxamidewith magnetic stirring for 8 h at 50 C and TLC (MeOH:EA = 1:1, v/v, Rf = 0.72) was used to monitor thereaction. Then, 6 M HCl was added into the solution andthe pH of the solution was adjusted to 1.0. Then, thesolution was extracted with ethyl acetate (5 9 10 mL).The organic phase was washed with brine (3 9 10 mL),dried with anhydrous Na2SO4, and was filtered to removethe drying agent. The ethyl acetate was removed by distillationunder reduced pressure to obtain the crudecompound of 7. Then, the crude 7 was dissolved intoEtOH (6 mL, 95%). The suspension was heated to refluxfor 30 min and was filtered to crystallize. The filtrate wascooled to 25-30 C which was kept for 4 h. The crystal ofpure 6-fluoro-3-hyroxypyrazine-2-carboxamide (7)(0.25 g, 60%) was obtained in open system.

The synthetic route of 356783-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Feng-Liang; Li, Cui-Qin; Xiang, Hao-Yue; Feng, Si; Chemical Papers; vol. 71; 11; (2017); p. 2153 – 2158;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

13134-38-8, name is 3,6-Dimethylpyrazin-2-amine, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C6H9N3

[0090] To a stuffed solution of 53 mg (0.427 mmol) of furan-2,5-dicarbaldehyde and 111 mg (0.90 1 mmol) of 3,6-dimethylpyrazin-2-amine in 5 mL of DCE was added 100 tL of acetic acid and approximately 500 mg of anhydrous Na2504. After 30 mm at rt under argon, the mixture was treated with 386 mg (1.82 mmol) of sodium triacetoxyborohydride, then was stirred further for 48 h. The mixture was treated with water (– 3 mL), excess satd. aq. NaHCO3, and EtOAc, and was stuffed an additional 1 h at rt. The mixture was extracted with EtOAc (3 x). The combined organic layers were washed with brine, dried over Na2504, and concentrated in vacuo. Purification by preparative TLC (90% EtOAc/hexanes) provided 10 mg of the title compound. MS (ESj: [M + H] 339.3; [M+Na] 361.4; MS (ES): EM-H] 337.4. ?H NMR: (500 MHz, CDC13) oe 7.62 (2H, s), 6.2 (2H, s), 4.63 (4H, d, J= 5 Hz), 4.55 (2H, br s), 2.35 (6H, s), 2.31 (6H,s). Also obtained was (5- (((3 ,6-dimethylpyrazin-2-yl)amino)methyl)furan-2-yl)methanol as a side product (See Example 8).

The synthetic route of 13134-38-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROPORE THERAPIES, INC.; WRASIDLO, Wolfgang; STOCKING, Emily, M.; (53 pag.)WO2016/40780; (2016); 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. 27825-21-4, name is Methyl 3-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H5ClN2O2

EXAMPLE II-23 In 15 mL of acetonitrile was dissolved 0.3 g of methyl 3-chloro-2-pyrazinecarboxylate. At an ice-cooled temperature, 10% fluorine gas (a fluorine gas diluted with nitrogen gas) was introduced at a rate of 45 ml per minute for a period of 18 minutes. Then, while elevating the temperature from the ice-cooled temperature to room temperature, nitrogen gas was introduced for one hour, and the reaction product was concentrated under reduced pressure. The oily product thus obtained was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=10:1] to obtain 0.03 g of methyl 3-chloro-6-fluoro-2-pyrazinecarboxylate as a colorless oily product. IR (neat) cm-1: 1736 1H-NMR (CDCl3) delta: 4.04(3H,s), 8.43(1H,d,J=8.3 Hz)

According to the analysis of related databases, 27825-21-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Toyama Chemical Co., Ltd.; US2003/130213; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem