Tag: M.W=200-300

Application of 24241-18-7, 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 54; Step 1; A suspension of 1 (3 g, 11.64 mmol) in 25% aq. NH4OH (15 mL) in sealed tube was heated at 110 C. for 16 h. After completion of reaction (reaction progress was monitored by TLC), the reaction mixture was partitioned between ethyl acetate-water (3¡Á50 mL). The combined extracts were washed with saturated brine, dried and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with 15% ethyl acetate-hexane to afford 2 as a yellow solid (2.1 g, 93%). MS m/z (ES): 189 (M+H)+.

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, 2-Amino-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; de Vicente Fidalgo, Javier; Hermann, Johannes Cornelius; Lemoine, Remy; Li, Hongju; Lovey, Allen John; Sjogren, Eric Brian; Soth, Michael; US2011/59118; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 369638-68-6, A common heterocyclic compound, 369638-68-6, name is tert-Butyl (5-methylpyrazin-2-yl)carbamate, molecular formula is C10H15N3O2, 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-Methylpyrazin-2-amine To a flask fitted with overhead stirrer, condenser, thermometer and nitrogen line was added tert-butyl (5-methylpyrazin-2-yl)carbamate (1.0 eq), and water (6.85 vols). The mixture was heated to 70 C. and trifluoroacetic acid (TFA) (1.2 eq) was added slowly drop-wise over 90-120 minutes. Water (0.22 vols) was added to wash the TFA into the flask. The reaction mixture was heated at 65-75 C. for at least 30 minutes, and then cooled to 15-25 C. Then 32% w/w sodium hydroxide (1.30 eq) was added drop-wise over 30-60 minutes maintaining the reaction temperature between 15-40 C. Water (0.22 vols) was added to wash the sodium hydroxide into the flask. N-Propylacetate (7.0 vols) was added and the mixture agitated for 45 minutes at 20 C. The layers were separated, the organic layer was retained and the aqueous layer was returned to the flask. N-Propylacetate (7.0 vols) was added and the mixture agitated for 45 minutes at 20 C. The layers were separated, the organic layer was retained and the aqueous layer was returned to the flask. This process was repeated twice. The combined organic layers were filtered through a filter containing silica (20% w/w) into a clean dry flask. The mixture was heated to 40 C. and then vacuum distilled to a final volume of 1.0-1.33 vols. Toluene (3.0 vols) was added, and the vacuum distillation continued at 40 C. to a final volume of 1.0-1.33 vols. This process was repeated twice. The resulting mixture was cooled to 5 C., and agitated for 1 hour at this temperature then filtered, washed with toluene (0.3 vols) at 0-5 C. The batch is slurry washed with toluene (1.0 vol) at 0-5 C. After drying at 45 C. overnight, the desired product was obtained as a solid (corrected yield typically 75%). 1H NMR delta (400 MHz CDCl3): 7.92 (s, 1H), 7.87 (s, 1H), 4.6 (bs, 2H), 2.40 (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; AstraZeneca AB; US2010/210621; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 622392-04-5 as follows. Safety of 2-Bromo-5-iodopyrazine

Preparation 11 : iert-Butyl (2S)-2-[5-(5-bromopyrazin-2-yl)-1 H-benzimidazol-2-yl]pyrrolidine-1 – carboxylateTo ieri-butyl (2S)-2-[5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-benzimidazol-2-yl]pyrrolidine-1- carboxylate obtained from Preparation 6 (500 mg, 1.21 mmol) and 2-bromo-5-iodopyrazine obtained from Preparation 10 (310 mg, 1 .10 mmol) in toluene (12.5 ml_) and ethanol (1.6 ml_), were added [1 ,1- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (50 mg, 55 muiotaetaomicronIota) and sodium carbonate (1.1 ml_, 1 M aqueous solution, 1.1 mmol). The reaction mixture was heated at 60 C for 16 hours. After this time, the resulting mixture was cooled to room temperature, diluted with ethyl acetate (30 ml_) and washed with water. The aqueous layer was extracted again with ethyl acetate. The combined organic extracts were dried over MgS04 and the solvent was evaporated under reduced pressure. The crude product obtained was purified by flash chromatography (ethyl acetate : dichloromethane, 1 : 1 ) to give the title compound as a yellow solid (385 mg).LCMS (run time = 5 minutes, System D): Rt = 2.92 minutes; m/z 444 and 446 [MH+]H NMR (400 MHz, CD3OD): delta = 8.40-7.00 (br, 5H), 5.10-5.00 (m, 1 H), 3.75 (m, 1 H), 3.55 (m, 1 H), 2.55-2.35 (m, 1 H), 2.15-1.95 (m, 3H), 1 .10 (s, 9H).

According to the analysis of related databases, 622392-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; TRAN, Thien Duc; WAKENHUT, Florian; WO2011/154871; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 52333-42-3,Some common heterocyclic compound, 52333-42-3, name is 7-Bromopyrido[2,3-b]pyrazine, molecular formula is C7H4BrN3, 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 105 Under nitrogen atmosphere, to a mixture of 7-bromopyrido[2,3-b]pyrazine (300 mg), methyl boronate (100 mg) and cesium carbonate (930 mg) were added dioxane (7.0 ml), bis(dibenzilidenacetone)-palladium (80.0 mg) and triphenylphosphine (87.0 mg), and the mixture was stirred at 100 C. for 2.5 hours. To the reaction solution was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted three times with ethyl acetate. The extracts were combined, washed with a saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=3/1?1/1?0/1?ethyl acetate/ethanol=10/1) to give 7-methyl-pyrido[2,3-b]pyrazine (125 mg, 60%). 1H NMR (CDCl3, 400 MHz) delta 9.06 (d, 1H, J=2.3 Hz), 9.02 (d, 1H, J=1.7 Hz), 8.91 (d, 1H, J=1.7 Hz), 8.24 (d, 1H, J=2.3 Hz), 2.65 (s, 3H).

The synthetic route of 52333-42-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokunaga, Teruhisa; Hume, William Ewan; Kitoh, Makoto; Nagata, Ryu; US2003/181496; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6966-01-4, These common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-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.

4- (PYRROLIDIN-1-YLSULFONYL) PHENYLBORONIC acid (0.33 g, 1.29 mmol), methyl 3-amino-6- BROMOPYRAZINE-2-CARBOXYLATE (0.25 g, 1.08 mmol; described in: H. Ellingson, J. Amer. Chem. Soc. 1949, 2798), K3PO3 (3 M, 1.1 mL, 3.2 mmol), and Pd (dppf) Cl2 (0.044 g, 54 JUMOL) were suspended in ethylene glycol dimethyl ether/water (1.5 : 0.5 mL) and heated in a microwave oven at 160 C for 10 min. The reaction was repeated 3 times. The combined product mixtures were evaporated with silica gel and the crude product was purified by chromatography on silica gel using a HEPTAN/ETHYLACETATE gradient as the eluent to give 0.96 g (82% yield) of the title compound: MS (ES) m/z 363 (M+1).

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/55009; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 173253-42-4, These common heterocyclic compound, 173253-42-4, name is 2-Amino-5-bromo-6-chloropyrazine, 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 5-bromo-6-chloropyrazin-2-amine (200 mg, 0.98 mmol, 1 eq.) in DMF (3 mL) was added 3-methyl pyrazole (312 mg, 3.8 mmol, 5.0 eq.) and Cs2CO3 (1.24 g, 3.8 mmol, 5.0 eq.). The reaction mixture was allowed to heat at 100 C. for 16 h. The progress of the reaction was monitored by TLC and LCMS The reaction mixture was diluted with water (30 mL) and extracted using ethyl acetate (2*50 mL). The separated organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by normal phase column chromatography to afford the desired product (16 mg, 54%). LCMS: 309 [M+1]+. 1H NMR: (400 MHz, DMSO-d6) delta 9.35 (s, 1H), 8.06 (s, 1H), 7.96 (d, J=1.32 Hz, 1H), 7.90 (d, J=8.77 Hz, 1H), 7.81 (d, J=2.19 Hz, 1H), 7.13 (dd, J=1.75, 8.77 Hz, 1H), 6.98 (s, 2H), 6.23 (d, J=2.19 Hz, 1H), 2.08 (s, 3H).

Statistics shows that 2-Amino-5-bromo-6-chloropyrazine is playing an increasingly important role. we look forward to future research findings about 173253-42-4.

Reference:
Patent; GiraFpharma LLC; PHAM, Son Minh; CHEN, Jiyun; ANSARI, Amantullah; JADHAVAR, Pradeep S.; PATIL, Varshavekumar S.; KHAN, Farha; RAMACHANDRAN, Sreekanth A.; AGARWAL, Anil Kumar; CHAKRAVARTY, Sarvajit; (120 pag.)US2019/23666; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-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 6966-01-4, Product Details of 6966-01-4

The compound 3-amino-6-bromopyrazine-2-carboxylic acid methyl ester 3a (20.0 g, 86.2 mmol) was added to a 500 mL three-necked flask, dioxane (40mL), HBr (200mL) and acetic acid (40mL), stirred and dissolved -5 C dropwise to the reaction system was added NaNO2 (19.6g, 285mmol), the solution was stirred at -5 C (20mL) acetic acid for 4 hours. The system was poured into a solution of Na2SO3 and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous sodium sulfate, and dried under reduced pressure using a rotary evaporator, purified by column to give the title compound 3b (12.0g, 40.8mmol), in a yield of 47.3%

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; Shanghai Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Qiang; Qu Minkai; Zhang Linli; Song Jinqian; Liu Lei; Chen Haiji; Liu Qiang; Wang Yijin; Ge Jian; (67 pag.)CN109535164; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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: 6966-01-4

00154] Step 1 : To a suspension of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (2.5 g, 10.8 mmol) in ethanol (50 mL) was added hydrazine hydrate (3.2 g, 3 mL, 64.6 mmol) and the reaction mixture heated at 70 C for 1.5 h forming a thick yellow solid. The reaction mixture was filtered and the solid washed with water (20 mL) and ethanol (40 mL). The solid was dried in vacuo to yield 3-amino-6-bromo-pyrazine-2-carbohydrazide (2.7 g, 94% yield) as a light yellow solid. LC/MS m/z 233.1 [M+H]+. XH NMR (400 MHz, DMSO-i?) delta 9.78 (s, 1H), 8.31 (s, 1H), 7.62 (s, 2H), 4.53 (d, J = 3.5 Hz, 2H).

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; BINCH, Haley, Marie; HURLEY, Dennis, James; CLEVELAND, Thomas; JOSHI, Pramod; FANNING, Lev Tyler, Dewey; PINDER, Joanne; O’DONNELL, Michael; VIRANI, Anisa, Nizarali; KNEGTEL, Ronald, Marcellus Alphonsus; DURRANT, Steven, John; YOUNG, Stephen, Clinton; PIERRE-HENRI; KAY, David; REAPER, Philip, Michael; WO2011/143426; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 32111-21-0,Some common heterocyclic compound, 32111-21-0, name is 2-Iodopyrazine, molecular formula is C4H3IN2, 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 A flask was charged with pinacol borobate (383.0 mg, 1.0 mmol), iodopyrazole (226.6 mg, 1.1 mmol), Pd(OAc)2 (11.2 mg, 0.05 mmol), TFP (46.4 mg, 0.2 mmol), K2CO3 (690.0 mg, 5 mmol), water (3 mL) and DME (2 mL). After 3 vacuum/argon cycles, the resulting mixture was heated to 80 C. 45 min later, HPLC revealed that all boronate disappeared. The area ratio of C-H, coupling product and dimer was about 3.3:85.3:11.4 on HPLC. After the reaction mixture was cooled down to room temperature, EtOAc (5 mL) was added. The aqueous layer was separated and extracted with EtOAc (2*10 mL). The combined organic extracts were washed with brine (10 mL), dried over Na2SO4, and concentrated in vacuo. The crude product was purified via silica gel chromatography to afford the indole (0.27 g, 81%). 1H NMR (300 HMz, CDCl3) delta 8.77 (2H, bs), 8.60 (1H, s), 8.16 (1H, s), 7.82-7.76 (2H, m), 3.96 (3H, s), 3.78 (3H, s), 3.20 (1H, m), 2.08-1.92 (6H, m), 1.72-1.69 (2H, m); 13C NMR (100 HMz, CDCl3) delta 168.0, 147.4, 146.6, 144.4, 143.2, 138.0, 135.3, 129.0, 124.2, 120.5, 120.3, 120.0, 112.4, 52.0, 37.3, 33.6, 31.3, 26.5.

The synthetic route of 32111-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/183752; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 76537-18-3, These common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-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.

A. 5-Chloro-3-(2-methylprop-1-en-1-yl)pyrazin-2-amine, 37a (0433) (0434) A mixture of 3-bromo-5-chloropyrazin-2-amine (41 g, 0.20 mol), 4,4,5,5-tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane (34 g, 0.19 mol), Pd(dppf)Cl2 (3.0 g, 4.1 mmol), K2CO3 (85 g, 0.62 mol,) in dioxane (600 mL) and water (100 mL) was stirred for 24 h at 80 C. under N2. The reaction was allowed to cool to RT and then quenched by the addition of 1 L of water/ice. The resulting solution was extracted with EtOAc (2¡Á2 L). The organic layers were combined, dried (Na2SO4) and concentrated. The resulting black oil was used in the next step without further purification. Mass Spectrum (LCMS, ESI pos.): Calcd. for C8H10ClN3: 184.1 (M+H)+; found: 184.1.

Statistics shows that 3-Bromo-5-chloropyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 76537-18-3.

Reference:
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Huang, Hui; Player, Mark R.; (53 pag.)US2016/9662; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem