Tag: M.W=200-300

Electric Literature of 24241-18-7,Some common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, molecular formula is C4H3Br2N3, 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-(ii): Synthesis of 6, 8-dibromoimidazo [1, 2-a] pyrazine:To a stirred solution of Intermediate-lOa (0.2 g, 0.79 mmol) in IPA (5niL) was added Chloro acetaldehyde (0.12 mL, 0.952 mmol), and stirred at 100C for 24h. After the reaction was completed, the reaction mixture was cooled RT, pale brown solid was precipitated out, filtered the solid dried under vaccum to get the desired product (150 mg, 53%); 1H NMR (400 MHz, DMSO-d6): oe 9.02(s, 1H), 8.24(s, 1H), 7.9(s, 1H); MS (ES) m/z 277.9 (M+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-3,5-dibromopyrazine, its application will become more common.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125410; (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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 3-amino-6-bromopyrazine-2-carboxylate

Methyl 3-AMINO-6-BROMO-2-PYRAZINE-CARBOXYLATE (14.3 g9 61.6 mmol; see Example 16 (a) above) was suspended in 40 % aqueous METHYLAMINE (350 mL) and the resulting mixture was stirred vigorously for 7 hours at room temperature. The precipitate was collected, washed with water, and dried to afford 3-amino-6-bromo- pyrazine-2-carboxylic acid methylamide as a yellow solid (12.7 g, 90 %). H NMR (300 MHz, DMSO-D6) S2. 77 (d, J= 3 Hz, 3 H), 7.70 (br s, 2 H), 8. 33 (s, 1 H), 8. 56 (q, J= 3 Hz, 1 H); 13C NMR (100 MHz, DMSO-d6) #27.84, 123.49, 127.69, 150.43, 156.04, 167.18.

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; BIOGEN IDEC MA INC.; WO2004/92177; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 486424-37-7, These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-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.

Example 11 : 3-(lH-Benzimidazol-2-yl)-5-(3-pyridyloxy)pyrazin-2-amine (Compound 11-12)SCompound 11-12 METHOD K:Step 1: 3-Amino-iV-(2-aminophenyl)-6-bromopyrazine-2-carboxamide[00169] To a solution of 3-amino-6-bromopyrazine-2-carboxylic acid (140 g, 0.64 mol), o- phenylenediamine (70 g, 0.65 mol) and TBTU (247 g, 0.77 mol) in DMF (1.5 L) at 0 C was added drop wise DIPEA (166 g, 1.29 mol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water and the resultant precipitate isolated by filtration and washed with water. The precipitate was dried at 50C to give the sub-title compound as a brown solid that wasused in the next step without further purification product (140 g, 70 % Yield). XH NMR (400 MHz, DMSO) delta 4.95 (br s, 2H), 6.59 (m, 1H), 6.79 (d, 1H), 6.95 (m, 1H), 7.30 (d, 1H), 7.70 (bs, 2H), 8.40 (s, 1H) and 9.65 (s, 1H) ppm; MS (ES+) 307.8.

Statistics shows that 3-Amino-6-bromopyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 486424-37-7.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus, Alphonsus; O’DONNELL, Michael; REAPER, Philip, Michael; WO2011/143419; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 330786-09-9, These common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, 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 3,5-dichloro-pyrazine-2-carboxylic acid methyl ester (1.20 g, 5.82 mmol) in dimethylformamide (12 ml) is added potassium carbonate (0.96 g, 6.98 mmol) at RT followed by the addition of morpholine (0.5 ml, 5.82 mmol). The resulting mixture is stirred at RT for 3 h. After completion of the reaction, the mixture is diluted with water (20 ml) and extracted with EtOAc (3 x 30 ml). The combined organic layers are washed with water (30 ml), brine (30 ml), dried over anhydrous sodium sulfate and evaporated in vacuo to get the crude product, which is purified by column chromatography (silica gel, 10% acetone/hexane) to yield 3-chloro-5-morpholin-4-yl-pyrazine-2-carboxylic acid methylester (1.10 g, 4.28 mmol, 73%).

Statistics shows that Methyl 3,5-dichloropyrazine-2-carboxylate is playing an increasingly important role. we look forward to future research findings about 330786-09-9.

Reference:
Patent; GRUeNENTHAL GMBH; LUCAS, Simon; KUHNERT, Sven; BAHRENBERG, Gregor; SCHROeDER, Wolfgang; WO2014/82739; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 344940-70-1, These common heterocyclic compound, 344940-70-1, name is 5-Bromo-3-phenylpyrazin-2-amine, 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.

[00184] To a solution of 5-bromo-3-phenylpyrazin-2-amine (26 mg, 0.1 mmol) and tert-butyl isopropyl(5-(tributylstannyl)thiazol-2-yl)carbamate (80 mg, 0.15 mmol) in DMF (0.4 mL) was added PdCl2(PPh3)2 (7 mg, 0.01 mmol) followed by DIPEA (0.044 mL, 0.25 mmol) and the reaction heated at 85 0C for 18h. The reaction mixture was cooled to room temperature and diluted with EtOAc (6 mL) and water (2 mL). the layers were separated and the aqueous layer further extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated via column chromatography (SiO2, 25% EtO Ac/heptane) to afford the product (44 mg, 100% yield).

The synthetic route of 344940-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/155389; (2009); 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. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 762240-92-6

A round bottom flask is charged with 2,4,5-thfluorophenylacetic acid (25 g),Meldrums acid (20.5 g), N,N-dimethylaminopyhdine (1.28 g), and acetonitrile (75 ml_). Diisopropylethylamine (47.28 ml_) is added drop-wise, while maintaining the temperature below 500C. The mixture is heated to 500C, followed by drop-wise addition of pivalolyl chloride (17.8 ml_) over about 45 minutes. The mixture is maintained at the same temperature with stirring for 3 hours, followed by addition of thazole hydrochloride (30 g) in one portion. Subsequently, thfluoroacetic acid (2.95 ml_) is added and the mixture is maintained at 55C for another 6 hours. The mixture is cooled to room temperature, followed by distillation to remove acetonitrile and afford a residue. Water (100 ml_) and ethyl acetate (500 ml_) are added to the residue, and the organic layer is separated. The organic layer is washed with 5% sodium bicarbonate, then brine solution (50 ml_), and is dried over sodium sulphate, followed by distillation at 400C to form a ketoamide, i.e., 4- oxo-4-[3-(thfluoromethyl)-5,6-dihydro[1 ,2,4]thazolo[4,3a]pyrazin-7(8H)-yl]-1 -(2,4,5- trifluorophenyl)butan-2-one. lsopropyl alcohol (75 ml_) and (R)-(+)-1 – phenylethylamine (18.64 ml_) are added and the mixture is heated to 45-50C for 4 hours. The isopropyl alcohol is distilled completely below 40C to form a residue. Dichloromethane (200 ml_) and water (100 ml_) are mixed with the residue, followed by separation of the organic layer. The aqueous layer is extracted with dichloromethane (200 ml_). The organic layers are combined, washed with brine, dried over sodium sulphate, and distilled to afford a residue, which, on purification results in the title compound (28.7g, 42.8% yield).

The synthetic route of 762240-92-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; BANDICHHOR, Rakeshwar; GUDIMALLA, Nagaraju; DWIVEDI, Namrata; CHETLURU, Kiran Kumar; GADE, Srinivas Reddy; MUVVA, Venkateswarlu; SRIVASTAVA, Bindu; WO2011/25932; (2011); A2;,
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. 17890-77-6, name is 3-Amino-6-bromopyrazine-2-carboxamide, A new synthetic method of this compound is introduced below., Computed Properties of C5H5BrN4O

Step 3: Synthesis of Intermediate D’ as described in the general scheme: 2,5-dibromo-3-amidopyrazine A mixture of C’ (200 g, 922 mM), aq. hydrobromic acid 47% (500 mL) and acetic acid (100 mL) is cooled to -10 C. Bromine (47.25 mL, 922 mM) is then added to the reaction mixture over 45 min at -10 C. A solution of sodium nitrite (190 g, 2.765 M) in water (400 mL) is then added over 2h, whilst maintaining the reaction mixture temperature below -5 C. Upon completion of the addition, the reaction mixture is further stirred for 30 min. A solution of sodium thiosulfate (250 g) in water (712 mL) is then added over 30 min forming a suspension. The solid is isolated by filtration, washed with water (400 mL*2) and dried at 50-55 C. under vacuum to afford crude D’. Crude D’ (186 g) is suspended in a solution of 2-butanone (93 mL) and hexane (279 mL) and then stirred at 30 C. for 1 hr. The solid is isolated by filtration, the cake is washed with a 1:3 mixture of 2-butanone (93 mL) and hexane (186 mL) and dried at 50 C. for 3 hrs to afford clean D’.

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; WIGERINCK, Piet Tom Bert Paul; ANDREWS, Martin James Inglis; De WEER, Marc Maurice Germain; SABOURAULT, Nicholas Luc; KLUGE, Stefan Christian; US2011/118269; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 486424-37-7, These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-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.

3-Amino-6-bromo -N- (3,4- difluorobenzyl) pyrazine-2-carboxamide: A mixture of 1.51 g 3-amino-6-bromo-2-carboxylic acid (6.93 mM mole), 30 ml dimethylformamide, 1.23 ml 3,4-difluoro benzylamine (10.4 mmol) and 2.40 ml N, N- diisopropylethylamine (13.8 mmol) in combination and stirred together, the batch and then 2.89 g (7-azo BTA) -N, N, N ‘, N’- tetramethyluronium hexafluorophosphate (7.60 mmol) and stirred for two hours , was added 250 ml of ethyl acetate and 150 ml of water, filtered, the organic phase was washed with 150 ml aqueous sodium bicarbonate wash, 50 ml brine, dried over magnesium sulfate drained, purified by flash column chromatography (0-50 % ethyl acetate; n-hexane), to collect 0.899 g of yellow powder (38%).

The synthetic route of 486424-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN MA INC.; SUNESIS PHARMACEUTICALS, INC.; ARNDT, JOSEPH; CHAN, TIMOTHY; GUCKIAN, KEVIN; KUMARAVEL, GNANASAMBANDAM; LEE, WEN-CHERNG; LIN, EDWARD YIN-SHIANG; SCOTT, DANIEL; SUN, LIHONG; THOMAS, JERMAINE; VAN VLOTEN, KURT; WANG, DEPING; ZHANG, LEI; ERLANSON, DANIEL; (469 pag.)TWI525093; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, 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. HPLC of Formula: C6H8ClF3N4

General procedure: A solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro [1,2,4]triazolo[4,3-a]pyrazine hydrochloride salt 9 (1.0 eq.) in dimethylformamide (DMF, 2e3 mL) was added potassium carbonate (2.5eq.) at 5 C and stirred for 15 min at room temperature. To this,various chloride derivatives (1.0 eq.) in DMF was added to reaction mixture at same temperature. The resultant reaction mixture was allowed to stir at room temperature for 24 h. The completion of the reaction was monitored on TLC (using 10% MeOH: DCM and ammonia as a modifier as mobile phase). The reaction mixture was poured into ice-cold water and extracted with ethyl acetate(2 x 15 mL). Organic layers were combined and the combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford crude material and crystallized it from methanol to get 3-(trifluoromethyl)-5,6,7,8-tetrahydro [1,2,4]triazolo [4,3-a]pyrazine derivatives (12f-12j) in good practical yield.

The synthetic route of 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jethava, Divya J.; Acharya, Prachi T.; Vasava, Mahesh S.; Bhoi, Manoj N.; Bhavsar, Zeel A.; Rathwa, Sanjay K.; Rajani, Dhanji P.; Patel, Hitesh D.; Journal of Molecular Structure; vol. 1184; (2019); p. 168 – 192;,
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. 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 87486-34-8

Example 114a (R)-5-bromo-3-(4-(1,4-dimethyl-3-oxopiperazin-2-yl)phenylamino)-1-methylpyrazin -2(1H)-one 114a A sealed tube equipped with a magnetic stirrer was charged with (R)-3-(4-aminophenyl)-1,4-dimethylpiperazin-2-one (1.08 g, 5 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (1.47 g, 5.5 mmol), diisopropylethylamine (1.94 g, 15 mmol), and iPrOH (20 mL). After three cycles of vacuum/argon flush, the mixture was heated at 110 °C overnight. After cooling down to room temperature, water (20 mL) was added to, and the mixture was extracted with ethyl acetate (50 mL X 2). The organic layer was separated, combined, dried over anhydrous sodium sulfate, and concentrated. The resulting residue was purified by silica gel column chromatography eluting with dichloromethane/methanol (10:1, V/V) to afford 114a (1.8 g, 90percent) as a red solid. LCMS: [M+H]+ 406

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 87486-34-8.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem