Category: 138402-36-5

Synthetic Route of 138402-36-5, 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. 138402-36-5, name is 3-(Aminomethyl)-5-chloropyridine, molecular formula is C6H7ClN2, 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.

To a suspension of 2-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)-6-(3,5-dimethylisoxazol-4-yl)quinazolin-4-ol, 2HCl (23.5 mg, 0.05 mmol) and bromotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate (46.6 mg, 0.10 mmol) in 1,4-dioxane (1 ml) was added Et3N (0.14 ml, 1.0 mmol). The mixture was stirred at rt for 2 h and then (5-chloropyridin-3-yl)methanamine (14.26 mg, 0.10 mmol) was added. The mixture was stirred at 50 C for another overnight. The mixture was concentrated, dissolved in DMF (2 mL), filtered and submitted for purification by semi-preparative HPLC to give N-((5-chloropyridin-3-yl)methyl)-2-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)-6-(3,5-dimethylisoxazol-4-yl)quinazolin-4-amine, 2TFA (1 mg, 1.34 mumol, 2.7 % yield). 1H NMR (400 MHz, DMSO-d6) delta 12.01 (s, 1H), 10.07 (s, 1H), 8.58 (d, J = 1.8 Hz, 1H), 8.51 (d, J = 2.3 Hz, 1H), 8.25 – 8.09 (m, 1H), 7.94 (d, J = 2.3 Hz, 1H), 7.79 (s, 1H), 7.69 (s, 1H), 4.82 (d, J = 4.5 Hz, 2H), 3.81-3.85 (m, 6H), 2.79 (s, 6H), 2.65-2.51 (m, 6H), 2.41 (s, 3H), 2.24 (s, 3H). (including one salt NH). LC-MS (Method 2): tR = 3.47 min, m/z (M+H)+ = 521.

According to the analysis of related databases, 138402-36-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Shyh-Ming; Urban, Daniel J.; Yoshioka, Makoto; Strovel, Jeffrey W.; Fletcher, Steven; Wang, Amy Q.; Xu, Xin; Shah, Pranav; Hu, Xin; Hall, Matthew D.; Jadhav, Ajit; Maloney, David J.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 21; (2018); p. 3483 – 3488;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 138402-36-5, 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. 138402-36-5, name is 3-(Aminomethyl)-5-chloropyridine, molecular formula is C6H7ClN2, 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.

To a suspension of 2-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)-6-(3,5-dimethylisoxazol-4-yl)quinazolin-4-ol, 2HCl (23.5 mg, 0.05 mmol) and bromotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate (46.6 mg, 0.10 mmol) in 1,4-dioxane (1 ml) was added Et3N (0.14 ml, 1.0 mmol). The mixture was stirred at rt for 2 h and then (5-chloropyridin-3-yl)methanamine (14.26 mg, 0.10 mmol) was added. The mixture was stirred at 50 C for another overnight. The mixture was concentrated, dissolved in DMF (2 mL), filtered and submitted for purification by semi-preparative HPLC to give N-((5-chloropyridin-3-yl)methyl)-2-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)-6-(3,5-dimethylisoxazol-4-yl)quinazolin-4-amine, 2TFA (1 mg, 1.34 mumol, 2.7 % yield). 1H NMR (400 MHz, DMSO-d6) delta 12.01 (s, 1H), 10.07 (s, 1H), 8.58 (d, J = 1.8 Hz, 1H), 8.51 (d, J = 2.3 Hz, 1H), 8.25 – 8.09 (m, 1H), 7.94 (d, J = 2.3 Hz, 1H), 7.79 (s, 1H), 7.69 (s, 1H), 4.82 (d, J = 4.5 Hz, 2H), 3.81-3.85 (m, 6H), 2.79 (s, 6H), 2.65-2.51 (m, 6H), 2.41 (s, 3H), 2.24 (s, 3H). (including one salt NH). LC-MS (Method 2): tR = 3.47 min, m/z (M+H)+ = 521.

According to the analysis of related databases, 138402-36-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Shyh-Ming; Urban, Daniel J.; Yoshioka, Makoto; Strovel, Jeffrey W.; Fletcher, Steven; Wang, Amy Q.; Xu, Xin; Shah, Pranav; Hu, Xin; Hall, Matthew D.; Jadhav, Ajit; Maloney, David J.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 21; (2018); p. 3483 – 3488;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 138402-36-5, 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.138402-36-5, name is 3-(Aminomethyl)-5-chloropyridine, molecular formula is C6H7ClN2, molecular weight is 142.5862, as common compound, the synthetic route is as follows.

To a rnixture of 6-brorno-2,4-dichloroquinazoline (1.946 g, 7 rnrnol) in THF (Volurne: 20 rnl) was added (5-chloropyridin-3-yl)rnethanarnine (0.998 g, 7.0 rnrnol) and then Et3N (1.463 rnl, 10.50 rnrnol) at rt. The rnixture was stirred at 0 00 for 15 rnin and then warrned to RT for 1.5 h (cornplete by TLC). The rnixture was poured into EtOAc/H20 (50 rnL/50 rnL). The aqueous layerwas extracted with EtOAc (50 rnL x 2). The cornbined organic layer was dried (Na2504) and filtered. After rernoval of solvent, the product was and sorne EtOAc (5-10 rnL), sonicated, and then added hexane (200 rnL) slowly. The solid was filtered and triturated with hexane and then dried to give 6-brorno-2-chloro-N-((5-chloropyridin-3-yl)rnethyl)quinazolin-4-arnine (2.31 g, 6.01 rnrnol, 86 % yield) as a solid.

The chemical industry reduces the impact on the environment during synthesis 138402-36-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; STROVEL, Jeffrey William; YOSHIOKA, Makoto; MALONEY, David J.; YANG, Shyh Ming; JADHAV, Ajit; URBAN, Daniel Jason; (334 pag.)WO2017/91661; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem