5-(1-Methylcyclopropyl)isoxazol-3-amine

Base Information

• Chemical Name: 5-(1-Methylcyclopropyl)isoxazol-3-amine
• CAS No.: 95924-26-8
• Molecular Formula: C7H10N2O
• Molecular Weight: 138.169
• European Community (EC) Number: 833-440-4
• Nikkaji Number: J3.151.281F
• Mol file: 95924-26-8.mol

Synonyms:95924-26-8;5-(1-methylcyclopropyl)-1,2-oxazol-3-amine;5-(1-methylcyclopropyl)isoxazol-3-amine;5-(1-methylcyclopropyl)isoxazol-3-ylamine;SCHEMBL1013280;VWRMBSADUPWJBG-UHFFFAOYSA-N;AKOS006349224;AT28127;DB-340485;EN300-1665568

Chemical Property of 5-(1-Methylcyclopropyl)isoxazol-3-amine

Chemical Property:

• PSA: 52.05000
• LogP: 1.88950
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 138.079312947
• Heavy Atom Count: 10
• Complexity: 145

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CC1)C2=CC(=NO2)N

Technology Process of 5-(1-Methylcyclopropyl)isoxazol-3-amine

There total 1 articles about 5-(1-Methylcyclopropyl)isoxazol-3-amine 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:

Reference yield:

methyl 1-methylcyclopropanecarboxylate (6206-25-3) → 5-(1-methylcyclopropyl)isoxazol-3-ylamine (95924-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 70 - 75 °C

1.2: pH 2

2.1: sodium hydroxide; hydroxylamine sulfate / ethanol; water / 80 °C / pH 7.5

With sodium hydride; hydroxylamine sulfate; sodium hydroxide; In tetrahydrofuran; ethanol; water; mineral oil;

Reference yield:

2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid (797755-07-8) + 5-(1-methylcyclopropyl)isoxazol-3-ylamine (95924-26-8) → N-(5-(1-methylcyclopropyl)isoxazol-3-yl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (1267856-42-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; 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 16h;

DOI:10.1016/j.bmcl.2015.07.023

Reference yield:

2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid (797755-07-8) + 5-(1-methylcyclopropyl)isoxazol-3-ylamine (95924-26-8) → 2-(4-(6-aminopyridin-3-yl)phenyl)-N-(5-(1-methylcyclopropyl)isoxazol-3-yl)acetamide (1267851-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / water; acetonitrile / 1 h / 90 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In water; N,N-dimethyl-formamide; acetonitrile; 2: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.bmcl.2015.07.023

upstream raw materials:

methyl 1-methylcyclopropanecarboxylate

Downstream raw materials:

N-(5-(1-methylcyclopropyl)isoxazol-3-yl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide

2-(4-(6-aminopyridin-3-yl)phenyl)-N-(5-(1-methylcyclopropyl)isoxazol-3-yl)acetamide

Refernces