Chemical compound
Imolamine Trade names Angolon, Angoril, Circuline, Irri-Cor, Irrigor, Coremax ATC code
Diethyl[2-(5-imino-3-phenyl-4,5-dihydro-1,2,4-oxadiazol-4-yl)ethyl]amine
CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.005.699 Formula C 14 H 20 N 4 O Molar mass 260.341 g·mol−1 3D model (JSmol )
CCN(CC)CCN2C(=N)O\N=C2\c1ccccc1
InChI=1S/C14H20N4O/c1-3-17(4-2)10-11-18-13(16-19-14(18)15)12-8-6-5-7-9-12/h5-9,15H,3-4,10-11H2,1-2H3
N Key:MGSPDRWOUCPKNZ-UHFFFAOYSA-N
N
N Y (what is this?) (verify)
Imolamine (INN , BAN ; brand names Angolon , Angoril , Circuline , Irri-Cor , Irrigor , Coremax ) is a coronary vasodilator which is used in the treatment of angina pectoris and as a local anesthetic .[1] [2]
Use patents:[3] [4]
Synthesis
Butalamine has very similar synthesis but is alkylated on the alternate nitrogen position.
Thieme Patent[5]
The reaction of benzoylchloride oxime [698-16-8] (2 ) with Cyanamide (3 ) gives 3-Phenyl-1,2,4-oxadiazol-5-amine [3663-37-4] (4 ). Alkylation with 2-chlorotriethylamine [100-35-6] (5 ) in the presence of KOH base occurs at the endocyclic ring nitrogen completing the synthesis of imolamine (6 ).
EFforts towards Onepot method (section 2.5 & 2.6).
References