Category: 1196152-38-1

Synthetic Route of 1196152-38-1, A common heterocyclic compound, 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, molecular formula is C5H2BrF3N2, 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 81N- (3,4-Dif [uoropheny[)-3-methy[-5-{[5- (trif[uoromethy[)pyrazin-2-y[]amino- 1 ,2-thiazo[e-4-carboxamide A mixture of 5-amino-N-(3,4-dif[uoropheny[)-3-methy[-1 ,2-thiazo[e-4-carboxamide [Intermediate 3] (100 mg, 0.37 mmo[, 1.0 eq), 2-bromo-5-(trif[uoromethy[)- pyrazine [CAS-RN: 1196152-38-1] (105 mg, 0.45 mmo[, 1.2 eq) and cesiumcarbonate (242 mg, 0.74 mmo[, 2.0 eq) in 4.0 mL dioxane/DMF (7/1) was p[aced ina microwave via[ that was f[ushed with argon. Then, pa[[adium(II) acetate (8 mg,0.04 mmo[, 0.1 eq) and Xantphos (21 mg, 0.04 mmo[, 0.1 eq) were added.Afterwards, the via[ was sea[ed and the reaction mixture was stirred at anenvironmenta[ temperature of 110 C for 4 h. On coo[ing, the reaction mixture was partitioned between ethy[ acetate and water. The organic phase was washed with brine and the phases were separated by the use of a Whatman fi[ter. The vo[ati[e components of the organic phase were removed in vacuo. Purification was conducted via preparative HPLC (Method A) to give 36 mg (22 % yie[d of theory) ofthe tit[e compound.UPLC-MS (Method 1): Rt = 1.36 mm; MS (ESIneg) m/z = 414 [M-H].1HNMR (400 MHz, DMSO-d6): oe [ppm] = 2.46 (s, 3H), 7.34-7.54 (m, 2H), 7.95 (dd, 1H), 8.82 (s, 1H), 8.91 (s, 1H), 10.53 (s, 1H), 11.46 (s, 1H).

The synthetic route of 1196152-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; PRECHTL, Stefan; SIEMEISTER, Gerhard; WENGNER, Antje Margret; ACKERSTAFF, Jens; NOWAK-REPPEL, Katrin; BADER, Benjamin; LIENAU, Philip; STOeCKIGT, Detlef; WO2014/118186; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1196152-38-1, 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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

1 ,1 -dimethylethyl (1 S,4S,6S)-4-(aminomethyl)-3-azabicyclo[4.1.0]heptane-3- carboxylate D29 (400 mg) and 2-bromo-5-(trifluoromethyl)pyrazine (401 mg, 1.767 mmol) were dissolved in DMF (2 ml) then sodium carbonate (375 mg, 3.53 mmol) was added and the mixture was heated to 50 0C for 2 hours. DMF was concentrated under vacuum and the residue was taken up with DCM (3 ml) and washed with NaHCO3 saturated solution (4 ml). The organic phase was filtered through a phase separator tube, concentrated under vacuum and purified by silica gel chromatography (Biotage SP- column size 25 g SNAP using Cy:EtOAc = 8:2 to 2:8 as eluent). It was recovered the title compound D30 (300 mg)

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-(trifluoromethyl)pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; ALVARO, Giuseppe; AMANTINI, David; CASTIGLIONI, Emiliano; DI FABIO, Romano; PAVONE, Francesca; WO2010/63662; (2010); 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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C5H2BrF3N2

example 3o (100 mg, 0.55 mmol), 2-Chloropyrimidine (76.3 mg, 0.67 mmol) and N,N- diisopropylethylamine (192 mu, 1.11 mmol) are dissolved in 1 ml of DMSO and the reaction mixture is heated in a microwave reactor 30 minutes at 120C. The crude product is partitioned between Et20 and water; the organic layer is then separated and concentrated under reduced pressure to obtain the title compound (158 mg). UPLC-MS (Method 2): Rt = 0.76 MS (ES+): m/z = 259 [M+H]+ . Example 37a is synthesized as described for example 28a using example 3r (70 mg, 0.35 mmol) instead of example 3o, 2-Bromo-5-(Trifluoromethyl)pyrazine (102 mg, 0.45 mmol) instead of 2-Chloropyrimidine, N,N-diisopropylethylamine (239 mu, 1.38 mmol) and 1 ml of DMSO. The mixture is heated in a microwave reactor during 30 minutes at 120C. The crude product is partitioned between Et20 and water then the organic layer is separated and concentrated under reduced pressure; the residue is purified by preparative HPLC-MS to obtain the title compound (70 mg, 44 % yield) as trifluoroacetate salt. UPLC-MS (Method 1): Rt = 0.90 MS (ES+): m/z = 349 [M+H]+

The synthetic route of 1196152-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)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. Recommanded Product: 1196152-38-1

Description 121: 1,1-dimethylethyl (lS,4S,6S)-4-({[5-(trifluoromethyl)-2- pyrazinylJoxyJmethylJ-S-azabicyclo^.l.OJheptane-S-carboxylate (D121); To a solution of 1,1-dimethylethyl (lR,4S,6R)-4-(hydroxymethyl)-3- azabicyclo[4.1.0]heptane-3-carboxylate D104 (120 mg) and 2-bromo-5-(trifluoromethyl)pyrazine D66 (120 mg) in DMF (2 ml) at 00C (ice bath) was added NaH (31.7 mg, 0.792 mmol) (gas evolution). The reaction mixture was slowly warmed to room temperature and stirred at room temperature for 1 hour. The reaction was quenched by a slow and careful addition of saturated aqueous solution of NaHCCb (40 ml). The organic phase was extracted with DCM (3×20 ml), the combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated to give the title compound D121 (150 mg) which was used in the next step without any purification.UPLC (Acid Final QC): rt = 0.89 minutes, peak observed: 274 (M+l – Boc), 374 (M+l) C17H22F3NsOs requires 373.

The synthetic route of 2-Bromo-5-(trifluoromethyl)pyrazine has been constantly updated, and we look forward to future research findings.

Some common heterocyclic compound, 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, molecular formula is C5H2BrF3N2, 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. Product Details of 1196152-38-1

To a suspension of Example 3B (0.08 g, 0.249 mmol) in N,N-dimethylformamide (0.5 mL, 6.46 mmol) were added N,N-diisopropylethylamine (0.174 mL, 0.996 mmol) and 2-bromo- 5-(trifluoromethyl)-pyrazine (0.068 g, 0.299 mmol). The reaction mixture was stirred overnight at 90 C, and then it was concentrate under reduced pressure at 50 C. The residue was purified by flash column chromatography on silica gel (12 g) eluted with heptane and ethyl acetate (0 to 100%) to give 40 mg of the title compound (37.3% yield) as a white solid. JH NMR (400 MHz, DMSO- ) delta ppm 8.78 (s, 1H), 8.59 (s, 1H), 8.44 (s, 1H), 7.99 (s, 1H), 7.55 (d, J = 8.8 Hz, 1H), 7.27 (d, J = 2.8 Hz, 1H), 6.99 (dd, J = 9.0, 2.9 Hz, 1H), 4.51 (s, 2H), 2.37 (s, 6H); 19F NMR (376 MHz, DMSO- ) delta ppm -64.83, -114.06; MS (ESI+) m/z 447 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1196152-38-1, its application will become more common.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)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 1196152-38-1, Safety of 2-Bromo-5-(trifluoromethyl)pyrazine

To a solution of ethyl 2-hydroxyacetate (0.167 mL, 1.762 mmol) in tetrahydrofuran (4 mL) at room temperature was added potassium teri-butoxide (1.850 mL, 1.850 mmol). After 10 minutes, 2-bromo-5-(trifluoromethyl)pyrazine (0.2g, 0.881 mmol) in tetrahydrofuran (4 mL) was added. The mixture was stirred at room temperature overnight. The reaction mixture was quenched by addition of water (10 mL), and extracted with ethyl acetate (3 x 30 mL). The organic phase was dried with MgSO/t, filtered and concentrated under reduced pressure. The residue was used in the next step without further purification (215 mg, 0.859 mmol, 98% yield).JH NMR (400 MHz, DMSO-19F NMR (376 MHz, DMSO- 6) delta ppm -65.37 MS (ESI+) m/z 251 (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-Bromo-5-(trifluoromethyl)pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; BROWN, Brian, S.; MURAUSKI, Kathleen; (673 pag.)WO2019/90069; (2019); 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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H2BrF3N2

Example 44k (300 mg, 0.8 mmol), 2-Chloro-5-(trifluoromethyl)pyrimidine (199 mg, 1.09 mmol) and N,N-diisopropylethylamine (287 mul, 1.67 mmol) are dissolved in 4 ml of anhydrous DMSO and heated in a microwave reactor during 30 minutes at 150C. The crude is partitioned between EtOAc and water, the organic layer is dried over anhydrous Na2S04 then concentrated under reduced pressure to obtain 360 mg of the title product. HPLC-MS (Method 10): Rt = 3. MS (ES+): m/z = 505 [M+H]+ . The enantiomers are obtained by HPLC using a chiral stationary phase. Method for separation: HPLC apparatus type: Waters 600 Pump; column: Daicel Chiralpack AD-H, 5.0 muiotaeta, 250 mm x 20 mm; method: eluent hexane/ IPA 70:30; flow rate: 15 mL/min, Temperature: 25 C; UV Detection: 254 nm Example of separation by chiral HPLC: Submitted to separation: 665 mg of Example 1 prepared as described above; Obtained: 157 mg of enantiomer 1 (Exp. 2) and 40 mg of enantiomer 2 (Exp. 3). Example 109 is synthesized as described for example 1 starting from example 44g (80 mg, 0.24 mmol) instead of example 44k, 2-Bromo-5-(trifluoromethyl)pyrazine (70 mg, 0.31 mmol) instead of 2-Chloro-5-(trifluoromethyl)pyrimidine, N,N-diisopropylethylamine (80 mu, 0.48 mmol) and 1 ml of anhydrous DMSO; the reaction mixture is heated during 30 minutes at 100C in a microwave reactor. After the work-up the crude is purified by Silica gel flash chromatography using EtOAc/hexane/MeOH 80:20: 1 as eluent to obtain the title compound (80 mg, 70% yield). HPLC-MS (Method 5): Rt = 2.95 min. MS (APCI+): m/z = 487 [M+H]+

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (2015); 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 1196152-38-1 as follows. Application In Synthesis of 2-Bromo-5-(trifluoromethyl)pyrazine

example 3o (100 mg, 0.55 mmol), 2-Chloropyrimidine (76.3 mg, 0.67 mmol) and N,N- diisopropylethylamine (192 mu, 1.11 mmol) are dissolved in 1 ml of DMSO and the reaction mixture is heated in a microwave reactor 30 minutes at 120C. The crude product is partitioned between Et20 and water; the organic layer is then separated and concentrated under reduced pressure to obtain the title compound (158 mg). UPLC-MS (Method 2): Rt = 0.76 MS (ES+): m/z = 259 [M+H]+ . Example 30a is synthesized as described for example 28a using example 3o (600 mg, 3.3 mmol), 2-Bromo-5-(Trifluoromethyl)pyrazine (907 mg, 4.0 mmol) instead of 2- Chloropyrimidine, N,N-diisopropylethylamine (1.1 ml, 6.7 mmol) and 8 ml of DMSO. The mixture is heated in a microwave reactor at 100C during 2.5 hours. The crude product is partitioned between EtOAc and water then the organic layer is separated and concentrated under reduced pressure; the residue is purified by Silica gel flash chromatography, using EtOAc/Cyclohexane 1 : 1 to EtOAc 100% as eluent, to obtain the title compound (800 mg, 72 % yield). HPLC-MS (Method 5): Rt = 3.21 MS (APCI+): m/z = 327 [M+H]+ .

According to the analysis of related databases, 1196152-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, A new synthetic method of this compound is introduced below., name: 2-Bromo-5-(trifluoromethyl)pyrazine

To a suspension of N-(3-aminobicyclo[l . l . l]pentan-l-yl)-2-(3,4- dichlorophenoxy)acetamide hydrochloride (0.08 g, 0.237 mmol, Example 2B) in N,N- dimethylformamide (0.5 mL, 6.46 mmol) was added N,N-diisopropylethylamine (0.166 mL, 0.948 mmol) followed by 2-bromo-5-(trifluoromethyl)pyrazine (0.065 g, 0.284 mmol). The reaction mixture was stirred overnight at 90 C. It was then concentrate under reduced pressure at 50 C. The residue was purified by flash column chromatography on silica gel (24 g) eluted with heptane and ethyl acetate (0 to 100%) to give 40 mg of the title compound (35.9% yield) as a white solid. JH NMR (400 MHz, DMSO-<) delta ppm 8.78 (s, 1H), 8.59 (s, 1H), 8.44 (s, 1H), 7.99 (s, 1H), 7.55 (d, J = 8.8 Hz, 1H), 7.27 (d, J = 2.8 Hz, 1H), 6.99 (dd, J = 9.0, 2.9 Hz, 1H), 4.51 (s, 2H), 2.37 (s, 6H). 19F NMR (376 MHz, DMSO-<) delta ppm -64.83; MS (ESI+) mJz 447 (M+H)+. 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; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); 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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Bromo-5-(trifluoromethyl)pyrazine

Example 44k (300 mg, 0.8 mmol), 2-Chloro-5-(trifluoromethyl)pyrimidine (199 mg, 1.09 mmol) and N,N-diisopropylethylamine (287 mul, 1.67 mmol) are dissolved in 4 ml of anhydrous DMSO and heated in a microwave reactor during 30 minutes at 150C. The crude is partitioned between EtOAc and water, the organic layer is dried over anhydrous Na2S04 then concentrated under reduced pressure to obtain 360 mg of the title product. HPLC-MS (Method 10): Rt = 3. MS (ES+): m/z = 505 [M+H]+ . The enantiomers are obtained by HPLC using a chiral stationary phase. Method for separation: HPLC apparatus type: Waters 600 Pump; column: Daicel Chiralpack AD-H, 5.0 muiotaeta, 250 mm x 20 mm; method: eluent hexane/ IPA 70:30; flow rate: 15 mL/min, Temperature: 25 C; UV Detection: 254 nm Example of separation by chiral HPLC: Submitted to separation: 665 mg of Example 1 prepared as described above; Obtained: 157 mg of enantiomer 1 (Exp. 2) and 40 mg of enantiomer 2 (Exp. 3). Example 110 is synthesized as described for example 1 starting from example 44b (60 mg of the corresponding hydrochloride, 0.15 mmol) instead of example 44k, 2-Bromo-5- (trifluoromethyl)pyrazine (42 mg, 0.19 mmol) instead 2-Chloro-5- (trifluoromethyl)pyrimidine, N,N-diisopropylethylamine (107 mu, 0.62 mmol) and 1 ml of anhydrous DMSO; the reaction mixture is heated during 30 minutes at 120C in a microwave reactor. The crude is purified by preparative HPLC-MS to obtain the title compound (24 mg, 32% yield) HPLC-MS (Method 10): Rt = 3.48 min. MS (ES+): m/z = 487 [M+H]+

According to the analysis of related databases, 1196152-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem