Mabuterol

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).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).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).

Mabuterol synthesis ^{[

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IUPAC nameCAS NumberChemSpiderChEMBLCompTox DashboardFormulaMolar massSMILESβ2 adrenoreceptor agonistClenbuterolCimaterolAdrenergic receptormodulatorsAmidephrineBuspironeCirazolineCorbadrineDeoxyepinephrine (epinine, N-methyldopamine)DesglymidodrineDipivefrineDopamineDroxidopa (L-DOPS)EpinephrineEtilefrineEtilevodopaEthylnorepinephrineIbopamineIndanidineIsomethepteneL-DOPA (levodopa)L-PhenylalanineL-TyrosineMelevodopaMetaraminolMethoxamineMethyldopaMidodrineNaphazolineNorepinephrineOctopamineOxymetazolinePhenylephrinePhenylpropanolamineSynephrineTetryzolineTiamenidineXP21279XylometazolineAbanoquilAjmalicineAlfuzosinAnisodamineAnisodineAtiprosinAtypical antipsychoticsbrexpiprazoleclozapineolanzapinequetiapinerisperidoneBenoxathianBeta blockersadimololamosulalolarotinololcarvediloleugenodilollabetalolBuflomedilBunazosinCorynanthineDapiprazoleDomesticineDoxazosinErgolinesacetergamineergotaminedihydroergotaminelisuridenicergolinetergurideEtoperidoneFenspirideHydroxyzineIndoraminKetanserinL-765,314MepiprazoleMetazosinMonatepilMoxisylyteNaftopidilNantenineNeldazosinNiaprazineNiguldipinePardoprunoxPelanserinPerlapinePhendioxanPhenoxybenzaminePhentolaminePhenylpiperazineantidepressantshydroxynefazodonenefazodonetrazodonetriazoledionePiperoxanPrazosinQuinazosinQuinidineSilodosinSpegatrineSpiperoneTalipexoleTamsulosinTerazosinTiodazosinTolazolineTetracyclic antidepressantsamoxapinemaprotilinemianserinTricyclic antidepressantsamitriptylineclomipraminedoxepinimipraminetrimipramineTrimazosinTypical antipsychoticschlorpromazinefluphenazineloxapinethioridazineUrapidilWB-4101Zolertine(R)-3-Nitrobiphenyline4-NEMDAmitrazApraclonidineBrimonidineClonidineDetomidineDexmedetomidineGuanabenzGuanfacineGuanoxabenzLofexidineMedetomidineMivazerolMoxonidineRilmenidineRomifidineTizanidineTolonidineVatinoxanXylazineAmesergideAptazapineAtipamezoleasenapinelurasidonepaliperidonezotepineAzapironesgepironeipsapironetandospironeBRL-44408EfaroxanEsmirtazapineFenmetozoleFluparoxanIdazoxanMirtazapineNAN-190PiribedilRauwolscineRotigotineSetiptilineSpiroxatrineSunepitronYohimbineAbediterolAlifedrineAmibegronArbutamineArformoterolBambuterolBefunololBitolterolBroxaterolBuphenineCarbuterolCarmoterolColterol