Mabuterol

Mabuterol is a selective β₂ adrenoreceptor agonist.^[1][2]

Mabuterol

Clinical data
Other names	Mabuterolum; PB 868Cl
Identifiers
IUPAC name 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(tert-butylamino)ethanol
CAS Number	56341-08-3
PubChem CID	3995
ChemSpider	3857
UNII	R4K19W6S7Q
ChEBI	CHEBI:135325
ChEMBL	ChEMBL86749
CompTox Dashboard (EPA)	DTXSID3048283
Chemical and physical data
Formula	C13H18ClF3N2O
Molar mass	310.75 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc1cc(cc(c1N)C(F)(F)F)C(O)CNC(C)(C)C
InChI InChI=1S/C13H18ClF3N2O/c1-12(2,3)19-6-10(20)7-4-8(13(15,16)17)11(18)9(14)5-7/h4-5,10,19-20H,6,18H2,1-3H3 Key:JSJCTEKTBOKRST-UHFFFAOYSA-N

Synthesis

Mabuterol synthesis^{[3][4][5][6][7]}

The halogenation of 2-(Trifluoromethyl)aniline [88-17-5] (1) with iodine and sodium bicarbonate resulted in 2-Amino-5-Iodobenzotrifluoride [97760-97-9] (2). Protection with acetic anhydride followed by nucleophilic aromatic displacement with copper(I)cyanide gave N-[4-cyano-2-(trifluoromethyl)phenyl]acetamide [175277-96-0] (3). Hydrolysis of the nitrile and the protecting group gave 4-amino-3-(trifluoromethyl)benzoic acid [400-76-0] (4). Halogenation with chlorine gave 4-Amino-3-Chloro-5-(Trifluoromethyl)Benzoic Acid [95656-52-3] (5). Halogenation of the acid with thionyl chloride gave 4-Amino-3-chloro-5-(trifluoromethyl)benzoylchloride [63498-15-7] (6). Treatment with diethyl malonate [105-53-3] gave the acetophenone and hence 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]ethanone [97760-76-4] (7). Halogenation with bromine in acetic acid led to 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-bromoethanone [97760-87-7] (8). Treatment with tert-butylamine [75-64-9] yielded 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(tert-butylamino)ethenone, CID:13355601 (9). Reduction of the ketone with sodium borohydride completed the synthesis of Mabuterol (10).

See also

• Clenbuterol
• Cimaterol
• Trantinterol (regioisomer)