Tag: M.W=100-200

Electric Literature of 36070-75-4, 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. 36070-75-4 name is 5-Chloropyrazine-2-carbonitrile, 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.

To a microwave vial 5-chloropyrazine-2-carbonitrile (34.6 mg, 0.248 mmol), rac- I -((2S,3R,4R)-4- amino-2,3-dimethyl-6-(tetrahyd ro-2H-pyran-4-yl)-3,4-dihyd roquinolin- I (2H)-yl)ethanone (for preparation see Intermediate 152, 37.5 mg, 0.124 mmol), and DIPEA (0.065 mL, 0.372 mmol) wereadded and the reaction irradiated in a microwave at 200 C for 30 mm. The reaction was purified directly by MDAP (Formic) to give a pale yellow solid. This solid was eluted through a NH2 SPE (5 g) with MeOH, the eluent was concentrated to give the product (22 mg, 0.054 mmol, 43.8%) as an orange/red solid. LCMS (2 mm Formic): Rt = 0.89 mi [MH] = 406.

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

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: 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, 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 486460-21-3, Formula: C6H7F3N4

44.0 g (0.50 mol, 1.0 eq) of 3-oxopropionic acid was dissolved in 220 g of dichloromethane solution, and N,N-dimethylformamide 0.36 g (0.021 mol, 0.01 eq) was added, and the chloride was added dropwise. Sulfuric acid 62.5g (0.525mol, 1.05eq), dripped, heated to backThe reaction was carried out for 6 hours, and the reaction of the raw material in the GC was completed. The temperature was lowered to 20 C or lower, 75.9 g (0.75 mol, 1.5 eq) of triethylamine was added dropwise, the temperature was lowered to 0 to 5 C, and 3-(trifluoromethyl)-5 was added. 1,7,8-Tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride 114.3 g (0.50 mol, 1 eq), stirred at room temperature for 2 hours, added 60 mL of water, The layer was extracted with methylene chloride (60 g×2), and the organic layer was combined and evaporated to dryness to give a crude product, which was recrystallized from a mixture of acetone/heptane 1:3 to obtain 98.6 g of compound (III).The yield was 75.3%, and the HPLC purity was 98.6%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Anhui Haikang Pharmaceutical Co., Ltd.; Zhang Xiaoshun; (9 pag.)CN108314688; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, 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. SDS of cas: 875781-43-4

To a stirred solution of2-bromo-5H-pyrrolo[2,3-b]pyrazine (1.0 g,5.05 mmol)inTHF (10 mL)at 0 oc was added NaH (225 mg,5.63 mmol,60%)and the mixture was stirred for30 min. Benzenesulfonyl chloride (0.72 mL,5.66 mmol)was added dropwise and the mixturestirred at room temperature for an additional2 h. The mixture was quenched with sat. aq. NH4Cl15 (30 mL)and extracted with EtOAc (30 mL x 2). The combined organic layers were dried overanhydrous Na2S04,filtered and concentrated in vacuo to give the title compound (1.4 g,82%)as a yellow solid that required no further purification. 1H NMR (400 MHz,CD30D)8 8.45 (s,1H),8.24 (d,J = 4.0 Hz,1H),8.20- 8.15 (m,2H),7.74- 7.67 (m,1H),7.64- 7.59 (m,2H),6.85 (d,J= 4.0 Hz,1H).

The synthetic route of 875781-43-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; WAI, John; LAI, Kwong Wah; WANG, Fei; (251 pag.)WO2017/205536; (2017); A2;,
Pyrazine – Wikipedia,
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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. 54608-52-5, name is 2-Hydrazinopyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Hydrazinopyrazine

Example 3: Preparation of (4aS,5aS)-methyl l-(pyrazin-2-yl)-4,4a,5,5a-tetrahydro-l/ – cyclopropa[4,5]cyclopenta[l,2-c]pyrazole-3-carboxylate (Formula (He)). To a nitrogen-purged 50-L reactor was charged (lS,5R)-bicyclo[3.1.0]hexan-2-one (2.0 kg, 20.81 mol), dimethyl oxalate (2.84 kg, 24.05 mol, 1.2 eq.), and methanol (1.53 kg). The mixture was stirred at 20-25C and sodium methoxide solution (25 wt% in methanol, 6.49 kg, 30.04 mol, 1.44 eq.) added slowly so as to keep the temperature of the reaction mixture below 40C. The internal temperature of the reaction mixture was kept between 35-40C and the mixture monitored by HPLC for the disappearance of starting material (i.e., (lS,5R)-bicyclo[3.1.0]hexan-2-one). The reactor contents were then cooled to 30C before adding 2-hydrazinylpyrazine (2.43 kg, 22.07 mol, 1.06 eq.) to the reactor. Thereafter, 6N HC1 (6.76 L) was charged slowly to the reactor while maintaining an internal temperature of 35-40C. The mixture was then stirred at 35-40C and monitored for reaction completion by HPLC. The reaction was considered complete when the diketo methyl ester intermediate of Formula (Ilc-i) was less than 3 area % as determined by HPLC The mixture was concentrated by distillation under vacuum at a jacket temperature of 25-50C until no appreciable distillate was observed. Water (19.3 kg) was charged to the reactor and the mixture concentrated by distillation under maximum vacuum at a jacket temperature of 25-50C until no appreciable distillate was observed. Water (9.65kg) was added to the reaction mixture and the mixture stirred at 20-25C for at least 1 hour. The mixture was filtered and the filter cake washed with water (2 x 9.65 kg). The solids were placed in a vacuum oven set at 45-55C and dried to a constant weight. The yield of (4aS,5aS)-methyl l-(pyrazin-2-yl)-4,4a,5,5a-tetrahydro- l/i-cyclopropa[4,5]cyclopenta[l,2- c]pyrazole-3-carboxylate was 3.09 kg (58%); NMR (DMSO- , 400 MHz): delta 0.42-0.45 (td, J = 4.5, 7.8 Hz, 1H), 1.25- 1.30 (m, 1H), 2.28-2.34 (m, 1H), 2.71 -2.74 (m, 1H), 2.77 (d, / = 16.0 Hz, 1H), 2.90 (dd, / = 6.5, 16.4 Hz, 1H), 3.83 (s, 3H), 8.61 (dd, / = 1.5, 2.6 Hz, 1H), 8.68 (d, J = 2.5 Hz, 1H), 9.16 (d, / = 1.40 Hz, 1H); 13C NMR (DMSO- , 100 MHz) delta 16.80, 17.06, 23.50, 26.18, 51.83, 129.28, 135.15, 139.57, 142.47, 142.89, 147.07, 154.47, 161.62.

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; ARENA PHARMACEUTICALS, INC.; PAL, Biman B.; MONTALBAN, Antonio Garrido; (0 pag.)WO2016/85941; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 297172-19-1, These common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine, 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.

5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine (1.0 g, 7.71 mmol) was dissolved in absolute ethanol (50 mL) and the solution was placed under a nitrogen atmosphere. Cyclohexanecarbaldehyde (1.86 mL, 15.4 mmol) was added and the reaction mixture was stirred 2 h at room temperature. Then it was cooled in an ice-bath and sodium triacetoxyhydroborate (6.54 g, 30.9 mmol) was added portionwise. Stirring was continued at room temperature overnight, after which the reaction mixture was concentrated and partitioned between dichloromethane and water. After separation of the layers, the aqueous layer was basified to pH -14. and it was extracted with dichioromethane three times. The combined extracts were dried over sodium sulfate, filtered and concentrated. Flash chromatography (gradient of methanol in dichloromethane) gave the title compound as a light yellow solid (1 .82 g).1H NMR (ODd3) 6 7.51 (s, 1 H), 6.78 (s, 1 H), 4.05 (t, J = 5.5 Hz, 2H), 3.61 (s, 2H),2.79 (t, J = 5.5 Hz, 2H), 2.32 (d, J = 7.2 Hz, 2H), 1.85 – 1.62 (m, 5H), 1.60 – 1.46 (m, 1H), 1.32-1.10 (m, 3H), 0.98-0.82 (m, 2H).LC/MS m/z 220 [M+H].

The synthetic route of 297172-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE S.A.; DIAZ-FERNANDEZ, Jose Luis; ALMANSA-ROSALES, Carmen; NIECZYPOR, Piotr; WO2015/91795; (2015); 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. 21279-64-1, name is 5-Chloropyrazine-2-carboxamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H4ClN3O

5-Chloropyrazinamide (1, 50 mg, 0.3173 mmol), potassiumfluoride (KF) (110.43 mg, 1.90 mmol) and tetra-n-butylammonium bromide (TBABr) (20.46mg, 0.064 mmol) were added to a 10 mL RBF and placed under vacuum for 1 hour to dry.After filling the RBF with N2, 10 mL of dry DMSO stored over molecular sieves was added tothe RBF. The reaction mixture was heated to 110 C and refluxed for 30 min under N2. Afterthe reaction was shown to be complete by TLC, the mixture was cooled to room temperature, diluted with iced water and then extracted with ethyl acetate. The organic layer was dried withMgSO4 and the solvent was evaporated by vacuum to yield crude product which was purifiedby CombiFlash chromatography using a silica column and petroleum ether and ethyl acetateas the eluent.GC-EI Mass. Calculated for C5H4FN3O (M·+) 141.11, found 141.11. Two fragments peakswere also observed: M-CONH2·+ (C4H2FN2·+), m/z = 97.07 and M-CONH+ (C4H2FN2H+),m/z = 98.08.1H NMR (400 MHz, CDCl3 and CD3OD): delta 9.00 (s, 1H), delta 8.36 (d, J = 7.8 Hz, 1H). 19FNMR (400 MHz, CDCl3 and CD3OD): delta 75.17 (d, J = 7.3 Hz). 13C NMR (500 MHz, CDCl3and CD3OD): delta 164.72 (s, 1′-C), delta 161.56 (d, J = 256.5 Hz, 5′-C), delta 142.41 (d, J = 12.8 Hz, 3′-C),delta 142.27 (d, 2′-C) delta 131.78 (d, J = 38.7 Hz, 6′-C)

The synthetic route of 21279-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Zhuo; Ordonez, Alvaro A.; Smith-Jones, Peter; Wang, Hui; Gogarty, Kayla R.; Daryaee, Fereidoon; Bambarger, Lauren E.; Chang, Yong S.; Jain, Sanjay K.; Tonge, Peter J.; PLoS ONE; vol. 12; 2; (2017);,
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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloropyrazine-2-carbonitrile

Weigh 3-chloropyrazine-2-carbonitrile (1.7 g, 12.48 mmol) into a 100 mL single-neck round bottom flask,40 mL of acetonitrile was added thereto, and the solution was dissolved and clarified with stirring at room temperature.Thereafter, cesium carbonate (8.1 g, 24.96 mmol) was slowly added in portions to the system.After the addition was completed, an acetonitrile (10 mL) solution in which N-deuterated methylmethanesulfonamide (2.1 g, 18.72 mmol) was dissolved was added dropwise to the system.After the dropping was completed, the system was transferred to an oil bath at 80 C and stirred under reflux.After 30 minutes, TLC monitored the consumption of raw materials completely.The oil bath was removed, and the system was allowed to cool to room temperature, followed by suction filtration, and the filter cake was rinsed with acetonitrile (100 mL) multiple times.The filtrates were combined, and the solvent was removed by rotary evaporation to obtain a crude product, which was then separated by column chromatography.1.1 g of N- (3-cyanopyrazin-2-yl) -N-deuterated methylmethanesulfonamide was obtained as a light brown oily liquid,Yield: 42.3%.

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; Chengdu Haichuang Pharmaceutical Co., Ltd.; Du Wu; Li Yu; Wen Kun; Li Xinghai; Chen Yuanwei; (20 pag.)CN110452229; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19847-12-2, name is Pyrazinecarbonitrile, 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 19847-12-2, category: Pyrazines

The synthesis of 5 was similar to that of 4, but with pzn(21.0 mg, 0.2 mmol) in place of pza. The resultant solution wasallowed to evaporate slowly in darkness at room temperature forseveral days to afford the product as block-shaped clear lightbrown crystals of 5. (Yield: 68%, based on silver). Anal. Calc. (found)for AgC11H8N3O3: C, 39.08 (38.97); H, 2.38 (2.42); N, 12.43(12.52)%. IR (KBr): m (cm1) = 3421 (s), 3294 (s), 3071 (s), 1657(s), 1549 (s), 1453 (m), 1403 (s), 1358 (s), 1256 (s), 1173 (m),1059 (m), 1021 (m), 804 (s), 740 (m), 671 (m), 625 (w), 562 (m),454 (m).

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

Reference:
Article; Huang, Hua-Qi; Wang, Dan-Feng; Zhang, Ting; Huang, Rong-Bin; Journal of Molecular Structure; vol. 1086; (2015); p. 99 – 108;,
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. 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4744-50-7

General procedure: Pyrazine-2,3-dicarboxylic anhydride (1.0 g, 6.7 mmol) was dissolved in tetrahydrofuran (40 mL)in an Erlenmeyer flask and the corresponding substituted aniline (6.7 mmol, 1 equiv.) was added in one dose. The reaction mixture was stirred for 1 hour at laboratory temperature. Water (30 mL) was added into the mixture followed by the saturated aqueous solution of NaHCO3 until pH 6 to form thecorresponding 3-(phenylcarbamoyl)pyrazine-2-carboxylic acid 1-18. Obtained crystals were filtered off and washed with water. The progress of the procedure was monitored by TLC eluted with thesystem water/butanol/acetic acid 5:4:1.

According to the analysis of related databases, 4744-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Semelkova, Lucia; Jano?cova, Petra; Fernandes, Carlos; Bouz, Ghada; Jand?Ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; Molecules; vol. 22; 9; (2017);,
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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, HPLC of Formula: C5H7Cl2N3

13a. Synthesis of N-((3-chloropyrazin-2-yl)methyl)-3-methyloxetane-3-carboxamideTo a stirred suspension of 2-aminomethyl-3-chloropyrazine hydrochloride (content 77%; 4.34 mmol, 0.81 g) in dichloromethane (150 ml) were added 3-methyl-3-oxetanecarboxylic acid (4.34 mmol, 0.504 g), triethylamine (9.56 mmol, 1.33 ml), 4-dimethylaminopyridine (0.434 mmol, 0.053 g) and 1-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.69 mmol, 1.67 g). After stirring for 16 hours at room temperature the suspension was filtered over decalite and the decalite was washed with dichloromethane. The combined filtrates were washed with 0.3 N hydrochloric acid (350 mL), 0.03 N hydrochloric acid (350 mL) and sodium hydrogencarbonate (aq). All aqueous layers were twice extracted with dichloromethane. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to give crude material. Solid sodium chloride was added to all aqueous layers and these were extracted five times with dichloromethane. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to give a second crop of crude material. The combined crude products were purified using chromatography (silica gel, ethyl acetate) to yield N-((3-chloropyrazin-2-yl)methyl)-3-methyloxetane- 3-carboxamide (0.58 g).H NMR (CDCl3, 400 MHz): delta 1.68 (s, 3H), 4.52 (d, J = 6 Hz, 2H), 4.76 (d, J = 5 Hz, 2H), 4.98 (d, J = 6 Hz, 2H), 7.13 (brs, 1 H), 8.35 (d, J = 2 Hz, 1 H), 8.47 (d, J = 2 Hz, 1 H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem