Technology Process of 5-{4-[1-(5-pyridazin-3-yl-[1,2,4]oxadiazol-3-yl)cyclobutyl]phenyl}pyrimidin-2-ylamine
There total 5 articles about 5-{4-[1-(5-pyridazin-3-yl-[1,2,4]oxadiazol-3-yl)cyclobutyl]phenyl}pyrimidin-2-ylamine which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
pyridazine-3-carboxylic acid;
With
triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 3h;
Inert atmosphere;
1-[4-(2-aminopyrimidin-5-yl)phenyl]-N-hydroxycyclobutanecarboxamidine;
In
N,N-dimethyl-formamide;
at 110 ℃;
for 4h;
Inert atmosphere;
DOI:10.1021/jm501185j
- Guidance literature:
-
Multi-step reaction with 2 steps
1.1: hydroxylamine / ethanol; water / 16 h / 80 °C / Inert atmosphere
2.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
2.2: 4 h / 110 °C / Inert atmosphere
With
hydroxylamine; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jm501185j
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere
1.2: 16 h / 0 - 20 °C / Inert atmosphere
2.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / N,N-dimethyl-formamide / 0.33 h / 90 °C / Inert atmosphere; Microwave irradiation; Sealed tube
3.1: hydroxylamine / ethanol; water / 16 h / 80 °C / Inert atmosphere
4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
4.2: 4 h / 110 °C / Inert atmosphere
With
bis-triphenylphosphine-palladium(II) chloride; hydroxylamine; sodium hydride; sodium carbonate; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
ethanol; water; N,N-dimethyl-formamide; mineral oil;
2.1: |Suzuki-Miyaura Coupling;
DOI:10.1021/jm501185j
