Tag: M.W=100-200

59303-10-5, name is 2-Chloro-5-methylpyrazine, 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. Recommanded Product: 59303-10-5

a reaction vessel 4-bromo-N-methylbenzamide (53.1 mg, 0.248 mmol), rac-1-((2S,3R,4R)-4- amino-2,3-dimethyl-6-(tetrahyd ro-2H-pyran-4-yl)-3,4-dihyd roquinolin- I (2H)-yl)ethanone (for apreparation see Intermediate 152, 37.5 mg, 0.124 mmol), sodium tert-butoxide (35.8 mg, 0.372 mmol), in 1,4-Dioxane (5 mL) were added. The solution was treated with Pd2(dba)3 (17.03 mg, 0.019 mmol) and DavePhos (9.76 mg, 0.025 mmol) and left to stir at 100 C for 2 h under N2. The reaction mixture was allowed to cool to rt and then filtered through celite and the celite washed with ethyl acetate. The combined filtrates were concentrated in vacuo to a crude orange/brown gum. This gumwas purified by MDAP (Formic) to give asolid. This solid was eluted through a NH2 SPE (5 g) with MeOH, the eluent was concentrated to give the product (17 mg, 0.039 mmol, 31.5%) as an off-white solid. LCMS (2 mm Formic): Rt = 0.83 mi [MH] = 436.

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;,
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Synthetic Route of 56423-63-3, 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. 56423-63-3, name is 2-Bromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

mixture of 3,3′,3″-(l,3,5,2,4,6-trioxatriborinane-2,4,6-triyl)tris(N-(4- (trifluoromethoxy)phenyl)benzamide) (Stage 5.1, 65 mg, 0.071 mmol), 2-bromopyrazine (63.6 mg, 0.4 mmol), Pd(PPh3)2Cl2 (8.42 mg, 0.012 mmol), Na2C03 (63.6 mg, 0.600 mmol), DME (299 muGamma), water (86 muGamma), and EtOH (42.8 mu) was stirred at 80C for 16 h. The RM was cooled, diluted with THF (4 mL), stirred for 2 h with Si-Thiol (Silicycle, 118 mg, 0.150 mmol), filtered and the filtrate was evaporated off under reduced pressure to give the crude product which was purified by flash chromatography (Redisep Silica gel column, 12 g, cyclohexane / EtOAc, from 20% to 75% EtOAc) to afford the title compound as white needles. UPLC-MS (Condition 1) tR = 2.66 min, m/z =360.0 [M+H]+, m/z =358.0 [M-H]”; XH-NMR (400 MHz, DMSO-d6) delta ppm 7.40 (d, J=8.6 Hz, 2 H) 7.67 – 7.77 (m, 1 H) 7.92 (d, J=9.0 Hz, 2 H) 8.08 (d, J=7.8 Hz, 1 H) 8.37 (d, J=7.8 Hz, 1 H) 8.67 – 8.71 (m, 2 H) 8.77 – 8.80 (m, 1 H) 9.38 (d, J=1.5 Hz, 1 H) 10.59 (s, 1 H).

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

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GROTZFELD, Robert Martin; JONES, Darryl Brynley; MANLEY, Paul; MARZINZIK, Andreas; MOUSSAOUI, Saliha; PELLE, Xavier Francois Andre; SALEM, Bahaa; SCHOEPFER, Joseph; WO2013/171641; (2013); A1;,
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Related Products of 122-05-4, 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. 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

5 mmol of (2FPpy)2Ir(Cl)2Ir(2FPpy)2, 25 mmol of pyrazine-2,5-dicarboxylic acid (Py2CA), and 50 mmol of potassium carbonate were mixed in 100 mL of 1,2-dichloroethane, and refluxed for 24 hours under a nitrogen atmosphere. After the reaction was complete, the solution was cooled down to about 50 C., and filtrated. The filtrated solution was purified by using column chromatography to thereby produce (2FPpy)2Ir(Py2CA)Ir(2FPpy)2 at a yield of 86%.

The chemical industry reduces the impact on the environment during synthesis Pyrazine-2,5-dicarboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SAMSUNG ELECTRONICS CO., LTD.,; US2008/269484; (2008); A1;,
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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. 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H5ClN2O2

To a solution of 0.10 g of methyl 6-chloropyrazine-2-carboxylate in 2.9 mL of dioxane, 65 mg of 2-furanboronic acid, 74 mg of lithium chloride, 0.57 g of cesium carbonate, 21 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl and 24 mg of tris(dibenzylideneacetone)dipalladium(0) were added, and the mixture was heated under reflux for 2 hours. To the reaction mixture, water and ethyl acetate were added, the organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with hexane:ethyl acetate = 87:13 to 83:17 to obtain 74 mg of methyl 6-(2-furyl)pyrazine-2-carboxylate as a white solid. 1H-NMR (CDCl3) delta: 4.05 (3H, s), 6.60 (1H, dd, J = 3.5, 1.8 Hz), 7.30-7.32 (1H, m), 7.62-7.65 (1H, m), 9.12 (1H, s), 9.12 (1H, s)

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; TOYAMA CHEMICAL CO., LTD.; Taisho Pharmaceutical Co. Ltd.; EP2022793; (2009); A1;,
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Application of 5521-55-1,Some common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
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Synthetic Route of 43029-19-2,Some common heterocyclic compound, 43029-19-2, name is 3-Aminopyrazin-2(1H)-one, molecular formula is C4H5N3O, 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: The pyrazin-2(1H)-one base (11a, 14, 19, 20, 21 or 23) (2 mmol)was added in 1,1,1,3,3,3-hexamethyl-disilazane (HMDS, 10 mL) andheated at 120 for 3 h. Then, the solvent was removed in vacuo asmuch as possible and the obtained residue was dissolved or suspendedin DCM (15 mL), followed by the addition of sugar donor (B or C,2.4 mmol, 1.2 eq.). SnCl4 (2.0 mmol, 1.0 eq.) was added dropwise to thesolution in an ice bath and the reaction mixture was stirred overnight atrt. The solution was diluted with DCM (50 mL), washed with water(20 mL×2), dried over Na2SO4 and concentrated in vacuum. Thecrude residue was purified by silica gel column chromatography to giveintermediates 24a-24e and 27a-27c, which were subsequently treatedwith K2CO3 (2 mmol, 2 eq.) in MeOH (15 mL) to give nucleosides 25 a-25e and 28a-28c.

The synthetic route of 43029-19-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Shuang; Xu, Mingshuo; Guo, Qi; Zhu, Fuqiang; Jiang, Xiangrui; Xie, Yuanchao; Shen, Jingshan; Bioorganic and Medicinal Chemistry; vol. 27; 5; (2019); p. 748 – 759;,
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These common heterocyclic compound, 19847-12-2, name is Pyrazinecarbonitrile, 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. Formula: C5H3N3

Alternatively, 2-pyrazinecarboxamidine hydrochloride can be prepared as follows: A solution of 2-pyrazinecarbonitrile (21 g, 200 mmol) in a mixture of 10 mL of methyl alcohol and 120 mL of diethyl ether is treated with hydrogen chloride gas at 0 C. The mixture is then stored at 5 C. for 3 days. The precipitates are collected by filtration and and dried. This solid is then suspended in 100 mL of ethyl alcohol and the mixture is treated with ammonium gas at 0 C. The mixture is then stored at 5 C. for 4 days, and filtered. Concentration of the filtrate gives 2-pyrazinecarboxamidine hydrochloride as a tan solid (2.8 g).

The synthetic route of Pyrazinecarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2005/75357; (2005); A1;,
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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. 22047-25-2, name is Acetylpyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 22047-25-2

General procedure: To a stirred solution of aldehyde (10mmol) (4-(dimethylamino)benzaldehyde, 4-(1-piperidinyl)benzaldehyde, 4-(4-morpholinyl)benzaldehyde or 4-(diphenylamino)benz-aldehyde) in EtOH (75mL), ketone (20mmol) (2-acetylpyridine, 2-acetylthiazole or 2-acetylpyrazine) was added. Then KOH (1.54g, 27.5mmol) and NH3 (aq) (35mL) were added to the reaction mixture. The solution was stirred at room temperature for 24h. The solid was collected by filtration and washed with H2O. Recrystallization from ethanol (1, 4, 7, 10) or toluene (2, 3, 5, 6, 8, 9, 11, 12) afforded a crystalline solid.

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

Reference:
Article; Palion-Gazda, Joanna; Machura, Barbara; Klemens, Tomasz; Szlapa-Kula, Agata; Krompiec, Stanis?aw; Siwy, Mariola; Janeczek, Henryk; Schab-Balcerzak, Ewa; Grzelak, Justyna; Ma?kowski, Sebastian; Dyes and Pigments; vol. 166; (2019); p. 283 – 300;,
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These common heterocyclic compound, 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, 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. Computed Properties of C8H12N2O

The obtained 7.5 g of TMP-OH (49.3 mmol) was dissolved in 50 ml of absolute ethanol to add active manganese dioxide.(6.4g, 73.6mmol) was oxidized and reacted in an oil bath at 84 C for 2 h. After the TLC reaction was completed,The reaction solution was carefully filtered with a five-layer filter paper while hot, and the manganese dioxide powder was removed.After filtration, a clear filtrate was obtained, which was evaporated to dryness under reduced pressure on a rotary evaporator. Wet loading column chromatography:The mobile phase EA:PE (1:5) was separated and purified, and the fraction was monitored by TLC. Collecting the compound 1a-4 fraction,Combine the same fraction and distill it to obtain a crystalline white solid.5.5g (36.7mmol),[M+H]+=151 is 1a-4 (TMP-CHO), yield 75%.

The synthetic route of (3,5,6-Trimethylpyrazin-2-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Xique Pharmaceutical Co., Ltd.; Wang Yuqiang; Yao Hui; Wu Chuanbin; Tao Liang; Sun Yewei; (27 pag.)CN103804309; (2019); B;,
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Reference of 13924-94-2, The chemical industry reduces the impact on the environment during synthesis 13924-94-2, name is Methyl 5-aminopyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

To a solution of Int-1 (100 g, 1.063 mmol)) in DME (400 mL) was added Int-2 (155 g, 1.595 mmol) at room temperature. The reaction mixture was heated to 85 C. and stirring was continued overnight. The volatiles were concentrated under reduced pressure, then residue was diluted with water (500 mL) and dichloromethane (500 mL). The pH was adjusted to neutral by using sat. NaHCO3. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified through silica gel column chromatography, eluted with ethyl acetate to afford Int-3 (40 g, 28.5%) as syrup. To a solution of Int-3 (40 g, 0.303 mol) in acetonitrile (200 mL) was added N-Iodo succinamide (81 g, 0.3636 mol) at room temperature, and then stirred for 1 hour. The reaction mixture was poured into water and stirred for 30 minutes. The precipitated solids were filtered and solids were triturated in ethyl acetate (1 L), filtered solid, and washed with ethyl acetate. Then filtrate was washed with 10% Na2CO3 solution (250 mL), water, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford Int-4 (18.1 g, 23%) as a solid. Mass (m/z): 259 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.43 (d, J=8 Hz, 1H), 7.69-7.53 (m, 2H), 7.23 (t, J=6.6 Hz, 1H), 2.42 (s, 3H). To a suspended solution of Int-5 (12 g, 46.51 mmol) in IPA: water (80 mL: 30 mL) was added Pd Cl2(dppf).DCM (7.5 g, 9.3 mmol), tertiary butyl amine (4.9 g, 69.76 mmol) and Na2CO3 (7.3 g, 69.76 mmol) at room temperature. The reaction mixture was heated to 100 C. and stirring was continued overnight. The reaction mixture was allowed to room temperature, and then diluted with dichloromethane (250 mL) and water. The organic layer was separated, washed with 10% Na2CO3 solution (75 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified through silica gel column chromatography, eluted product with ethyl acetate to afford Int-6 (4.8 g, 42.4%) as a solid. Mass (m/z): 244 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.51 (t, J=5 Hz, 2H), 7.71 (s, 1H0, 7.63-7.55 (m, 2H), 7.34 (t, J=7 Hz, 1H), 6.94 (t, J=7 Hz, 1H), 2.43 (s, 3H). To a solution of Int-7 (1 g, 5.797 mmol) in THF (10 mL) was added 4-methoxy benzyl amine (1.98 g, 14.49 mmol) at room temperature and, then stirred overnight. The reaction mixture was filtered, concentrated under reduced pressure. The residue was purified through silica gel column chromatography, eluted product with 50% ethyl acetate/dichloromethane to afford Int-8 (800 mg, 50.6%) as a solid. Mass (m/z): 274 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.6 (s, 1H), 8.61-8.42 (brs, 1H), 8.01 (s, 1H), 7.23 (d, J=8.5 Hz, 2H), 6.83 (d, J=8.4 Hz, 2H). To a solution of Int-8 (800 mg, 2.925 mmol) in trifluoro acetic acid (5 mL) was stirred for 1 hour at 60 C. The reaction mixture was allowed to room temperature, and then quenched with solid sodium bicarbonate. The reaction mixture was diluted with ethyl acetate and water. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure rotavapour to afford Int-9 (350 mg, 78%) as a solid. Mass (m/z): 154 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.51 (s, 1H), 8.7.83 (s, 1H), 7.39 (brs, 2H), 3.79 (s, 3H). To a solution of Int-6 (1.58 g, 6.535 mmol) in 1,4-dioxane (25 mL) was added palladium acetate (238 mg, 1.045 mmol), Xantpos (498 mg, 1.045 mmol), Int-9 (1 g, 6.535 mmol) and cesium carbonate (3.21 g, 9.802 mmol) at room temperature. The reaction mixture was heated to 100 C. and stirring was continued for 18 hours. The reaction mixture was concentrated under reduced pressure, then residue was diluted with ethyl acetate. The precipitated solids were filtered, then washed with water (25 mL) and dried under vacuum. The solids were purified through silica gel column chromatography, eluted product with 3% methanol/dichloromethane to afford Int-10 (200 mg, 8.5%) as a solid. Mass (m/z): 361 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 10.8 (brs, 1H), 9.06 (s, 1H), 8.09 (s, 1H), 8.59-8.4 (m, 2H), 8.01 (s, 1H), 7.6 (d, J=7.4 Hz, 1H), 7.7.29-7.2 (m, 2H), 6.98 (t, J=7 Hz, 1H), 3.81 (s, 3H). To a solution of Int-10 (200 mg, 0.555 mmol) in methanol (4 mL) and dichloromethane (10 mL) was added hydroxyl amine solution (aqueous 50%) (4 mL) and reaction mixture was stirred for 20 minutes at 0 C. Then sodium hydroxide solution (3 mL) was added and the reaction mixture was allowed to room temperature, then stirred for 5 hours. The volatiles were concentrated under reduced pressure, then adjusted pH to neutral by using 1N HCl at 0 C. The precipitated solids were filtered, washed with water, dichloromethane and hexanes to afford the title compound (150 mg, 75%) as a solid. Mass (m/z): 362 [M++1]. (1H NMR 200 MHz (dmso-d6): delta 10.96 (brs, 1H), 9.01 (s, 1H), 8.72 (s, 1H), 8.54 (d, J=6.6 Hz, 1H), 8.47 (d, J=5.4 Hz, 1H), 7.99 (s, 1H), 7.6 (d, J=8.8 Hz, 1H), 7.33 (t, J=7.6 Hz, 1H), 7.24 (d, J=3.8 Hz, 1H), 6.99 (t, J=7 Hz, 1H), 6.42 (s,…

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

Reference:
Patent; Melvin, JR., Lawrence S.; Graupe, Michael; Venkataramani, Chandrasekar; US2010/29638; (2010); A1;,
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