Category: 135900-33-3

Synthetic Route of 135900-33-3, 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. 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, The 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.

0383] To a solution of 8-chloroquinoline-7-carboxylic acid Int-56 (Example 166) (0.139 g, 0.674 mmol) in DMF (5 mL) was added DIPEA (0.49 mL 2.808 mmol), followed by HATU (0.42 g, 1.123 mmol) at 0 C, and the reaction mixture was stirred at 0 C for 15 min. Then 6- (trifluoromethoxy)pyridin-3 -amine (0.1 g, 0.561 mmol) was added to reaction mixture at 0 C. The reaction mixture was stirred at r.t. for 16 hrs. After completion of the reaction, the reaction mixture was diluted with water (10 mL) and extracted with Ethyl Acetate (2×50 mL). Combined organic layers were washed with water (2×30 mL), brine (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crude product was purified by column chromatography (100-200 silica gel) using 50% Ethyl Acetate in Hexane as eluent to afford 50 mg (24% yield) of 8-chloro-N-(6-(trifluoromethoxy)pyridin-3-yl)quinoline-7-carboxamide 169 as an off-white solid. 1H-NMR (400 MHz, DMSO-d6): delta 11.08 (s, 1H), 9.12 (dd, J = 4.4, 1.6 Hz, 1H), 8.68 (d, J = 2.4 Hz, 1H), 8.55 (J = 8.4, 1.6 Hz, 1H), 8.37 (dd, J = 8.8, 2.4 Hz, 1H), 8.13 (d, J = 8.4 Hz, 1H), 7.79 (d, J = 8.8 Hz, 1H), 7.75 (dd, J= 8.4, 4.0 Hz, 1H), 7.38 (d, J= 8.8 Hz, 1H); MS (ESI) m/z 368.24 [M+H]+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 135900-33-3, Adding some certain compound to certain chemical reactions, such as: 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine,molecular formula is C6H5F3N2O, 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 135900-33-3.

[0293] Compound Int-5 (Example 122) (90 mg, 0.43 mmol, 1.0 eq) and 6- (trifluoromethoxy)pyridin-3-amine (84 mg, 0.47 mmol, 1.1 eq) were dissolved in DMF (3 mL), and the resulting mixture was cooled down to 0 C. Then HATU (181 mg, 0.47 mmol, 1.1 eq) and DIPEA (0.16 mL, 0.868 mmol, 2.0 eq) were added to the reaction mixture at 0 C. The reaction mixture was allowed to warm up to room temperature, and stirred at room temperature for 3 hrs. The progress of the reaction was monitored by LCMS and TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water. The formed solid was filtered, washed and dried in vacuo to give 40 mg of the desired compound 128 as an off-white solid in 25% yield. 1H NMR (400 MHz, DMSO-de): delta 11.12 (s, 1H), 9.03-9.02 (dd, J = 4.4 Hz, 2.0 Hz, 1H), 8.68-8.69 (d, J = 2.4 Hz, 1H), 8.46-8.44 (d, J = 7.6 Hz, 1H), 8.39-8.36 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 8.30-8.31 (m, 2H), 7.70- 7.67 (dd, J = 8.4 Hz, 4.0 Hz, 1H), 7.39-7.37 (d, J = 8.8 Hz, 1H). 99.45% purity by LCMS; m/z =368.11 [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. 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 135900-33-3, 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. 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, The 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.

0383] To a solution of 8-chloroquinoline-7-carboxylic acid Int-56 (Example 166) (0.139 g, 0.674 mmol) in DMF (5 mL) was added DIPEA (0.49 mL 2.808 mmol), followed by HATU (0.42 g, 1.123 mmol) at 0 C, and the reaction mixture was stirred at 0 C for 15 min. Then 6- (trifluoromethoxy)pyridin-3 -amine (0.1 g, 0.561 mmol) was added to reaction mixture at 0 C. The reaction mixture was stirred at r.t. for 16 hrs. After completion of the reaction, the reaction mixture was diluted with water (10 mL) and extracted with Ethyl Acetate (2×50 mL). Combined organic layers were washed with water (2×30 mL), brine (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crude product was purified by column chromatography (100-200 silica gel) using 50% Ethyl Acetate in Hexane as eluent to afford 50 mg (24% yield) of 8-chloro-N-(6-(trifluoromethoxy)pyridin-3-yl)quinoline-7-carboxamide 169 as an off-white solid. 1H-NMR (400 MHz, DMSO-d6): delta 11.08 (s, 1H), 9.12 (dd, J = 4.4, 1.6 Hz, 1H), 8.68 (d, J = 2.4 Hz, 1H), 8.55 (J = 8.4, 1.6 Hz, 1H), 8.37 (dd, J = 8.8, 2.4 Hz, 1H), 8.13 (d, J = 8.4 Hz, 1H), 7.79 (d, J = 8.8 Hz, 1H), 7.75 (dd, J= 8.4, 4.0 Hz, 1H), 7.38 (d, J= 8.8 Hz, 1H); MS (ESI) m/z 368.24 [M+H]+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 135900-33-3, Adding some certain compound to certain chemical reactions, such as: 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine,molecular formula is C6H5F3N2O, 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 135900-33-3.

[0293] Compound Int-5 (Example 122) (90 mg, 0.43 mmol, 1.0 eq) and 6- (trifluoromethoxy)pyridin-3-amine (84 mg, 0.47 mmol, 1.1 eq) were dissolved in DMF (3 mL), and the resulting mixture was cooled down to 0 C. Then HATU (181 mg, 0.47 mmol, 1.1 eq) and DIPEA (0.16 mL, 0.868 mmol, 2.0 eq) were added to the reaction mixture at 0 C. The reaction mixture was allowed to warm up to room temperature, and stirred at room temperature for 3 hrs. The progress of the reaction was monitored by LCMS and TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water. The formed solid was filtered, washed and dried in vacuo to give 40 mg of the desired compound 128 as an off-white solid in 25% yield. 1H NMR (400 MHz, DMSO-de): delta 11.12 (s, 1H), 9.03-9.02 (dd, J = 4.4 Hz, 2.0 Hz, 1H), 8.68-8.69 (d, J = 2.4 Hz, 1H), 8.46-8.44 (d, J = 7.6 Hz, 1H), 8.39-8.36 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 8.30-8.31 (m, 2H), 7.70- 7.67 (dd, J = 8.4 Hz, 4.0 Hz, 1H), 7.39-7.37 (d, J = 8.8 Hz, 1H). 99.45% purity by LCMS; m/z =368.11 [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. 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 135900-33-3, 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. 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine. A new synthetic method of this compound is introduced below.

[0292] Compound Int-8 (100 mg, 0.53 mmol, 1.0 eq) and 6-(trifluoromethoxy)pyridin- 3-amine (190 mg, 1.06 mmol, 2.0 eq) were dissolved in DMF (3.0 mL) and the reaction mixture was cooled down to 0 C. HATU (221 mg, 0.58 mmol, 1.1 eq) and DIPEA (136 mg, 1.06 mmol, 2.0 eq) were added to the reaction mixture at 0 C. The reaction mixture was allowed to warm up to room temperature, and stirred at room temperature for 4 hrs. The progress of the reaction was monitored by LCMS and TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water. The formed solid was filtered, washed and dried under vacuum to give 40 mg of the desired compound 127 as a pale-yellow solid in 21% yield. 97.88% purity as determined by HPLC at 215 nm. 1H NMR (400 MHz, DMSO-d6): delta 10.97 (s, 1H), 8.94 (dd, J = 4.4 Hz, 1.6 Hz, 1H), 8.72 (d, J = 2.4 Hz, 1H), 8.40 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 8.34 (d, J = 7.6 Hz, 1H), 8.20 (s, 1H), 7.91 (s, 1H), 7.60 (dd, J = 8.4 Hz, 4.4 Hz, 1H), 7.37 (d, J = 8.8 Hz, 1H), 2.57 (s, 3H). ESI m/z =348.27 [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,135900-33-3, its application will become more common.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 135900-33-3, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.

A mixture of Example 235C (0.095 g, 0.350 mmol), PyBOP ((1H- benzo[(i] [l ,2,3]triazol-l-yl)oxy)tri(pyrrolidin-l-yl)phosphonium hexafluorophosphate(V)) (0.219 g, 0.420 mmol), 6-(trifluoromethoxy)pyridin-3-amine (0.075 g, 0.420 mmol), and triethylamine (0.073 mL, 0.525 mmol) in N,N-dimethylformamide (DMF) (3 mL) was stirred for 3 hours. The reaction mixture was quenched with brine and saturated NaHC(, and extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried over (1679) MgSO/t, filtered, and concentrated. The residue was purified on a 12 g column using the Biotage Isolera One flash system eluted with heptanes/ethyl acetate (7:3 to 6:4) to provide the title compound (65.1 mg, 43%). MS (ESI+) nt/z 432.3 (M+H)+.

Statistics shows that 135900-33-3 is playing an increasingly important role. we look forward to future research findings about 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 135900-33-3, 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. 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, The 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.

A solution of Br2 (0.25 mL, 4.87 mmol) in HO Ac (3 mL) was added dropwise to a stirring solution of 6-(trifluoromethoxy)pyridin-3-amine (400 mg, 2.25 mmol) in EtOH (15 mL) and HO Ac (1.5 mL) at 0C under a nitrogen atmosphere. After addition was complete, the reaction was warmed to room temperature and was allowed to stir for an additional 15 hours. The reaction mixture was concentrated. DCM (30 mL) and saturated aqueous NaHC03 (20 mL) were added to the crude residue. The aqueous layer was extracted with DCM (50 mL x 3). The combined organic layers were dried over Na2S04, filtered and concentrated. The crude residue was purified by column chromatography (0-10% EtOAc in petroleum ether) to give 2,4- dibromo-6-(trifluoromethoxy)pyridin-3-amine (670 mg, yield: 89%) as light yellow solid. 1H NMR (400 MHz, CDCl3): d = 7.18 (s, 1H), 4.59 (s, 2H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; GENENTECH, INC.; STAFFORD, Jeffrey, A.; VEAL, James, M.; TRZOSS, Lynnie, Lin; MCBRIDE, Christopher; PASTOR, Richard, M.; STABEN, Steven, Thomas; STIVALA, Craig; VOLGRAF, Matthew; (200 pag.)WO2020/18970; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 135900-33-3, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.

[0294] A stirred solution of 7-bromo-6-fluoroquinoline Int-6 (Example 123) (100 mg, 0.442 mmol), 6-(trifluoromethoxy)pyridin-3-amine (157 mg, 0.884 mmol, 2.0 eq) and Na2CC>3 (112 mg, 0.884 mmol) in dry acetonitrile (2 mL) was degassed with Argon gas in a microwave vessel for 15 min. Then Mo(CO)6 (117 mg, 0.442 mmol, 1.0 eq), T3u3PHBF4 (15.3 mg, 0.05 mmol 0.12 eq) and Pd(OAc)2 (10 mg, 0.044 mmol, 0.1 eq) were added to this mixture, and degassing was continued for additional 10 min. The reaction mixture was irradiated in microwave at 90 C for 2 hrs. The progress of the reaction was monitored by LCMS and TLC. Upon completion, the reaction mixture was concentrated in vacuo. The crude product was purified by silica gel column chromatography using 50% EtOAc in petroleum ether as eluent to give 25 mg (16% yield) of the desired compound 129 as a pale-yellow solid. 99.2 % HPLC purity at 215 nm. 1H NMR (400 MHz, CDC13): delta 9.03- 9.02 (dd, J = 4.0 Hz, 1.6 Hz, 1H), 8.97-8.99 (d, J = 7.6 Hz, 1H), 8.59 (s, 1H), 8.55 (s, 1H), 8.47-8.49 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 8.45-8.46 (d, J = 2.4 Hz, 1H), 8.18 (d, J = 8.4 Hz, 1H), 7.61-7.64 (d, J = 12.8 Hz, 1H), 7.56-7.52 (dd, J = 8.4 Hz, 4.0 Hz, 1H), 7.12-7.10 (d, J = 8.0 Hz, 1H). 99.7% purity by LCMS; MS (ESI) m/z =352.14 [M+H]+.

Statistics shows that 135900-33-3 is playing an increasingly important role. we look forward to future research findings about 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 135900-33-3, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.

A mixture of Example 235C (0.095 g, 0.350 mmol), PyBOP ((1H- benzo[(i] [l ,2,3]triazol-l-yl)oxy)tri(pyrrolidin-l-yl)phosphonium hexafluorophosphate(V)) (0.219 g, 0.420 mmol), 6-(trifluoromethoxy)pyridin-3-amine (0.075 g, 0.420 mmol), and triethylamine (0.073 mL, 0.525 mmol) in N,N-dimethylformamide (DMF) (3 mL) was stirred for 3 hours. The reaction mixture was quenched with brine and saturated NaHC(, and extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried over (1679) MgSO/t, filtered, and concentrated. The residue was purified on a 12 g column using the Biotage Isolera One flash system eluted with heptanes/ethyl acetate (7:3 to 6:4) to provide the title compound (65.1 mg, 43%). MS (ESI+) nt/z 432.3 (M+H)+.

Statistics shows that 135900-33-3 is playing an increasingly important role. we look forward to future research findings about 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 135900-33-3, 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. 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, The 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.

A solution of Br2 (0.25 mL, 4.87 mmol) in HO Ac (3 mL) was added dropwise to a stirring solution of 6-(trifluoromethoxy)pyridin-3-amine (400 mg, 2.25 mmol) in EtOH (15 mL) and HO Ac (1.5 mL) at 0C under a nitrogen atmosphere. After addition was complete, the reaction was warmed to room temperature and was allowed to stir for an additional 15 hours. The reaction mixture was concentrated. DCM (30 mL) and saturated aqueous NaHC03 (20 mL) were added to the crude residue. The aqueous layer was extracted with DCM (50 mL x 3). The combined organic layers were dried over Na2S04, filtered and concentrated. The crude residue was purified by column chromatography (0-10% EtOAc in petroleum ether) to give 2,4- dibromo-6-(trifluoromethoxy)pyridin-3-amine (670 mg, yield: 89%) as light yellow solid. 1H NMR (400 MHz, CDCl3): d = 7.18 (s, 1H), 4.59 (s, 2H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; GENENTECH, INC.; STAFFORD, Jeffrey, A.; VEAL, James, M.; TRZOSS, Lynnie, Lin; MCBRIDE, Christopher; PASTOR, Richard, M.; STABEN, Steven, Thomas; STIVALA, Craig; VOLGRAF, Matthew; (200 pag.)WO2020/18970; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem