Tilisolol

Tilisolol (INN, trade name Selecal) is a beta blocker.^[1]

Tilisolol

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (RS)-4-[3-(tert-butylamino)-2-hydroxypropoxy]-2-methylisoquinolin-1-one
CAS Number	85136-71-6 Y 62774-96-3 (hydrochloride)
PubChem CID	5474
ChemSpider	5275
UNII	QUF41MF56G
KEGG	D08598 Y
CompTox Dashboard (EPA)	DTXSID0043846
Chemical and physical data
Formula	C17H24N2O3
Molar mass	304.390 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES CC(C)(C)NCC(COC1=CN(C(=O)C2=CC=CC=C21)C)O
InChI InChI=1S/C17H24N2O3/c1-17(2,3)18-9-12(20)11-22-15-10-19(4)16(21)14-8-6-5-7-13(14)15/h5-8,10,12,18,20H,9,11H2,1-4H3 Key:TWVUMMQUXMYOOH-UHFFFAOYSA-N
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Synthesis

Thieme ChemDrug Synthesis:^[2] Patent:^[3] Precursor:^[4] Sino:^[5] HPLC:^[6]

The methanolysis of Phthalic anhydride [85-44-9] (1) gives Methyl hydrogen phthalate [4376-18-5] (2). Schotten-Baumann amidation with Methyl sarcosinate [5473-12-1] (3) gives Methyl 2-[(2-methoxy-2-oxoethyl)-methylcarbamoyl]benzoate, PC11644670 (4). Intramolecular lactamization with sodium methoxide afforded Methyl 4-hydroxy-2-methyl-1-oxoisoquinoline-3-carboxylate, PC54684295 (5). In lye saponification followed by decarboxylation occurred to give 4-hydroxy-2-methylisoquinolin-1(2H)-one [30236-50-1] (6). Treatment with Epichlorhydrin [106-89-8] (7) in the presence of base led to 2-Methyl-4-[(oxiran-2-yl)methoxy]isoquinolin-1(2H)-one [62775-08-0] (8). Opening of the oxirane ring with tert-Butylamine [75-64-9] (9) completed the synthesis of Tilisolol (10).