Extended knowledge of 7170-01-6

The synthetic route of 3-Methyl-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

7170-01-6, 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

Step A Synthesis of 8-methoxy-2-methyl-4-(5-methyl-l//-l,2,4-triazol-l-yl)quinoline and 8- methoxy-2-methyl-4-(3 -methyl- H- 1 ,2,4-triazol- 1 -yl)quinoline4-chloro-8-methoxy-2- methylquinoline (100 mg, 0.481 mmol) was reacted with 3-methyl- IH-l, 2,¡¤ 4-triazole (46.0, 0.554 mmol) according to the synthesis of 4-(4-fluoro- 1 /Y-pyrazol- 1 -yl)-8-mcthoxy-2-mcthylquinolinc to give a mixture of the title compounds. MS (m/z): 255.3 [M+H+] Step B Synthesis of 2-methyl-4-(3-methyl-l//-l,2,4-triazol-l-yl)quinolin-8-ol and 2-methyl- 4-(5-methyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolin-8-ol (0284) A mixture of 8-mcthoxy-2-mcthyl-4-(5-mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolinc and 8- mcthoxy-2-mcthyl-4-(3-mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolinc (153 mg, 0.602 mmol) was demethylated according to the synthesis of 4-(4-fluoro-l//-pyrazol-l-yl)-2-methylquinolin-8-ol to give a mixture of the title compounds. MS (m/z): 241.1 [M+H+] Step C. Synthesis of (5)-2-(l-(3-chloro-5-fluoro-2-((2-methyl-4-(5-methyl-l//-l,2,4-triazol-l- yl)quinolin-8-yloxy)methyl)phenyl)ethyl)isoindoline- 1 ,3-dione and (5)-2-(l -(3-chloro-5-fluoro-2- ((2-methyl-4-(3 -methyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolin-8-yloxy)methyl)phenyl)ethyl)isoindoline- l,3-dione (0286) A mixture of 2-mcthyl-4-(3-mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinol in-8-ol and 2-methyl-4-(5- mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinol in-8-ol (48.3 mg, 0.201 mmol) was reacted with (5)-2-(l-(3- chloro-2-(chloromethyl)-5-fluorophenyl)ethyl)isoindoline-l,3-dione (70.7 mg, 0.201 mmol) according to the synthesis of (5)-2-(l-(3-chloro-5-fluoro-2-((4-(4-fluoro-l/7-pyrazol-l-yl)-2- methylquinolin-8-yloxy)methyl)phenyl)ethyl)isoindoline-l,3-dione to give a mixture of the title compounds. MS (m/z): 556.4 [M+H+] Step D. Synthesis of (5′)- 1 -(3-chloro-5-fluoro-2-((2-mcthyl-4-(5-mcthyl- 1 H- 1 ,2,4-triazol- 1 – yl)quinolin-8-yloxy)methyl)phenyl)ethanamine and (5)- 1 -(3-chloro-5-fluoro-2-((2-methyl-4-(3- methyl- H- 1 ,2,4-triazol- 1 -yl)quinolin-8-yloxy)methyl)phenyl)ethanamine (0287) A mixture of (S)-2-( 1 -(3-chloro-5-fluoro-2-((2-mcthyl-4-(5-mcthyl- 1 H- 1 ,2,4-triazol- 1 – yl)quinolin-8-yloxy)methyl)phenyl)ethyl)isoindoline- 1 ,3-dione and (5)-2-(l -(3-chloro-5-fluoro-2- ((2-methyl-4-(3 -methyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolin-8-yloxy)methyl)phenyl)ethyl)isoindoline- l,3-dione (111 mg, 201 miho) was deprotected according to the synthesis of (5)-l-(3-chloro-5- fluoro-2-((4-(4-fluoro- l/ -pyrazol- 1 -yl)-2-methylquinolin-8-yloxy)methyl)phenyl)ethanamine to give the title compounds. MS (m/z): 448.3 [M+Na+] Step E. Synthesis of (5)-7V-(l-(3-chloro-5-fluoro-2-((2-methyl-4-(5-methyl-l//-l,2,4-triazol- l-yl)quinolin-8-yloxy)methyl)phenyl)ethyl)-2-(difluoromethoxy)acetamide and (S)-N-( 1 -(3- chloro-5-fluoro-2-((2-methyl-4-(3 -methyl- H- 1 ,2,4-triazol- 1 -yl)quinolin-8- yloxy)methyl)phenyl)ethyl)-2-(difluoromethoxy)acetamide (0289) A mixture of (/S’)- 1 -(3-chloro-5-fluoro-2-((2-mcthyl-4-(5-mcthyl- 1 H- 1 ,2,4-triazol- 1 – yl)quinolin-8-yloxy)methyl)phenyl)ethanamine and (5)- 1 -(3-chloro-5-fluoro-2-((2-methyl-4-(3- mcthyl- 1 H- 1 ,2,4-triazol- 1 -yl)quinolin-8-yloxy)mcthyl)phcnyl)cthanaminc (19 mg, 43 mhio) was reacted with 2-(difluoromethoxy)acetic acid (7.2 mg, 56 mhio) according to the synthesis of (R)- N-((S)- 1 -(3-chloro-5-fluoro-2-((4-(4-fluoro- 1 /7-pyrazol- 1 -yl)-2-methylquinolin-8- yloxy)methyl)phenyl)ethyl)-2-hydroxypropanamide and purified by HPLC to yield (5′)-/V-( l -(3- chloro-5-fluoro-2-((2-methyl-4-(5-methyl- IH- 1 ,2,4-triazol- 1 -yl)quinolin-8- yloxy)methyl)phenyl)ethyl)-2-(difluoromethoxy)acetamide (MS (m/z): 534.2 [M+H+]) and ( S)-N – (1 -(3 -chloro-5-fluoro-2-((2-methyl-4-(3 -methyl- H- 1 ,2,4-triazol- 1 -yl)quinolin-8- yloxy)methyl)phenyl)ethyl)-2-(difluoromethoxy)acetamide (MS (m/z): 534.0 [M+H+])

The synthetic route of 3-Methyl-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARVARIS B.V.; GIBSON, Christoph; SAUPE, Joern; AMBROSI, Horst-Dieter; HAUSTEDT, Lars Ole; (99 pag.)WO2019/101906; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics