Category: 1196152-38-1

Application 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

Related Products 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

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.

1,1 -dimethyl ethyl (lS,4S,6S)-4-ethynyl-3-azabicyclo[4.1.0]heptane-3-carboxylate D17 (150 mg), 2-bromo-5-(trifluoromethyl)pyrazine (154 mg, 0.678 mmol), DIPEA (0.592 ml, 3.39 mmol), Pd[(C6H5)3P]4 (78 mg, 0.068 mmol) and copper(I) iodide (25.8 mg, 0.136 mmol) were collected together and dissolved in DMF (5 ml).The reaction was stirred at 23 C for 3 hours.A saturated solution of NaHC03 (20 ml) was added and the aqueous layer was back extracted with Et20 (3 x 10 ml). The collected organic layers were washed with brine (3 x 5 ml), dried over Na2S04, filtered, and concentrated under vacuum to give the crude product. The crude product was purified by silica gel chromatography (SNAP KP-Sil 25g cartridge; eluted with Cy/EtOAc 5 CV from 100% Cy to 90/10, 5 CV 90/10).Evaporation of the fractions gave the title compound D18 (140 mg).UPLC (IPQC): rt = 1.38 minutes, peak observed: 312 [M+l- C(CH3)3]

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

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89607; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)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. Application In Synthesis of 2-Bromo-5-(trifluoromethyl)pyrazine

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. 1H NMR (400 MHz, DMSO-d6) 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-d6) delta ppm -64.83, -114.06; MS (ESI+) m/z 447 (M+H)+.

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

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1196152-38-1,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.

[((1R,4S,6R)-3-{[6-methyl-3-(2-pyrimidinyl)-2-pyridinyl]carbonyl}-3-azabicyclo[4.1.0]hept-4-yl)methyl]amine D25 (80 mg) and 2-bromo-5-(trifluoromethyl)pyrazine (67.4 mg, 0.297 mmol) were dissolved in DMF (2 ml) then sodium carbonate (52.4 mg, 0.495 mmol) was added and the mixture was heated to 50 C. for 2 hours. DMF was evaporated under vacuum and the residue was dissolved in DCM (4 ml) and washed with NaHCO3 saturated solution (4 ml). The organic phase was filtered through a phase separator tube, concentrated under vacuum and the resulting crude product was purified by SCX Chromatography (column size 5 g). Another purification was performed by silica -NH chromatography (Biotage SP-column size 25 g using Cy_EtOAc=5:5 to EtOAc as eluent). It was recovered the title compound E45 (30 mg). UPLC: (Acid Final_QC): rt=0.78 and 0.79 minutes (two rotamers), peaks observed: 470 (M+1). C23H22F3N7O requires 469. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.91-8.82 (m, 2H), 8.36 (d, 1H), 8.20-7.86 (m, 3H), 7.47 (t, 1H), 7.36 (d, 1H) 4.40 (d, 1H), 3.81-3.55 (m, 2H), 3.49-3.35, (m, 2H), 2.38-2.30 (br. s., 3H), 1.80-1.65 (m, 2H), 1.15-1.06 (m, 1H), 1.03-0.91 (m, 1H), 0.80-0.71 (m, 1H), 0.29-0.19 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-(trifluoromethyl)pyrazine, its application will become more common.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1196152-38-1, 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.

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 34 is synthesized as described for example 1 starting from example 44f (80 mg, 0.22 mmol) instead of example 44k, 2-Bromo-5-(trifluoromethyl)pyrazine (75 mg, 0.33 mmol) instead of 2-Chloro-5-(trifluoromethyl)pyrimidine, N,N-diisopropylethylamine (75 mu, 0.44 mmol) and 1 ml of anhydrous DMSO. The reaction mixture is heated in a microwave reactor at 130C during 30 minutes. After the work-up, the crude product is purified by Silica gel flash chromatography using cyclohexane/EtOAc 20:80 to 0: 100 as eluent to obtain the title compound (83 mg, 74 % yield). HPLC-MS (Method 5): Rt = 2.96 min MS (APCI+): m/z = 505 [M+H]+ .

Statistics shows that 2-Bromo-5-(trifluoromethyl)pyrazine is playing an increasingly important role. we look forward to future research findings about 1196152-38-1.

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. Product Details of 1196152-38-1

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 26 is synthesized as described for example 1 starting from example 44k (70 mg, 0.18 mmol), 2-Bromo-5-(trifluoromethyl)pyrazine (60 mg, 0.26 mmol) instead of 2- Chloro-5-(trifluoromethyl)pyrimidine, N,N-diisopropylethylamine (60 mu, 0.35 mmol) and 1 ml of anhydrous DMSO. The reaction mixture is heated in a microwave reactor during 30 minutes at 150 C. After the work-up, the crude product is purified by preparative HPLC-MS to obtain the title compound (43 mg, 48 % yield). HPLC-MS (Method 10): Rt = 3. MS (ES+): m/z = 505 [M+H]+ .

The synthetic route of 2-Bromo-5-(trifluoromethyl)pyrazine 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

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

Step 25 A: 2-[(3R.5R)-3.5-dimethylpiperazin-l -yll-5-(trifluoromethyl)pyrazine (0923) To a solid mixture of (2R,6R)-2,6-dimethylpiperazine dihydrochloride (0924) (0.08 g, 0.44 mmol, 1.0 eq), sodium fert-butoxide (0.21 g, 2.2 mmol, 5.0 eq) and bis(tri- ter/-butylphosphine)palladium(0) (34 mg, 0.07 mmol, 0.15 eq) was added dioxane (4 mL) followed by 2-bromo-5-(trifluoromethyl)pyrazine (0.10 g, 0.44 mmol, 1.0 eq) and the reaction mixture stirred at 50C overnight. The resulting suspension was filtered thru a pad of celite using EtOAc and concentrated. Silica gel column (24 g) was loaded using methylene chloride and run using an increasing gradient of MeOH (0-20%) in methylene chloride over 25 min. Following concentration of the product eluents, 2- [(3R,5R)-3,5-dimethylpiperazin-l-yl]-5-(trifluoromethyl)pyrazine 25a (0.09 g, 0.33 mmol, 75%) was isolated as a yellow oil.

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

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; HARRIOTT, Nicole; PAGANO, Nicholas; (135 pag.)WO2017/79641; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1196152-38-1, 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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of N-(3-aminobicyclo[1.1.1]pentan-1-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. 1H NMR (400 MHz, DMSO-d6) 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-d6) delta ppm -64.83; MS (ESI+) m/z 447 (M+H)+.

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

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); 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., SDS of cas: 1196152-38-1

bis(triphenylphosphine)palladium(II) chloride (21.40 mg, 0.030 mmol), triphenylphosphine (15.99 mg, 0.061 mmol), TEA (4.5 ml, 32.3 mmol), 2-bromo-5-(trifluoromethyl)pyrazine (346 mg, 1.524 mmol) and copper(I) iodide (11.61 mg, 0.061 mmol) were collected together in a round bottomed flask. The mixture was stirred for 30 minutes and then 1,1- dimethylethyl (lR,4S,6R)-4-ethynyl-3-azabicyclo[4.1.0]heptane-3-carboxylate D5 (337 mg) was added. The reaction was stirred at room temperature for 2 hours.A saturated solution of H4CI (10 ml) was added and the aqueous layer was back extracted with diethyl ether (3 x 10 ml). The collected organic layers were washed with brine (3 x 5 ml), dried over Na2S04, filtered, and concentrated under vacuum to give the crude product. The crude product was purified by silica gel chromatography (SNAP KP-Sil 25g cartridge; eluted with Cy/EtOAc 5CV from 100% Cy to 90/10, 5 CV 90/10).Collection and evaporation of the fractions gave the title compound D27 (300 mg).UPLC (GEN_QC_SS) rt = 1.02 minutes, peak observed: 312 [M-C(CH3)3] Ci8H20F3N3O2 requires: 368.

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; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89607; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem