合成路线1

4-Bromo-3-fluorotoluene (I) is converted into the Grignard reagent (II) with magnesium in boiling Et2O, and subsequently added to cyclopropylacetonitrile (III) to produce ketone (IV). Condensation of (IV) with hydroxylamine affords oxime (V), which is further alkylated with benzyl bromide to yield the O-benzyl oxime (VI). Asymmetric reduction of oxime (VI) with borane in the presence of the aminoalcohol chiral auxiliary (VII) provides the (S)-amine (VIII). Reaction of amine (VIII) with ammonium thiocyanate and benzoyl chloride, followed by treatment with hydrazine hydrate, gives rise to the thiourea (IX). Friedel-Crafts acylation of 4-chloro-2-methoxytoluene (X) with 2-bromopropionyl bromide (XI) employing AlCl3 furnishes the bromo ketone (XII). Then, condensation of thiourea (IX) with bromo ketone (XII) in the presence of Et3N in boiling EtOH gives rise to the aminothiazole (XIII). Finally, alkylation of the amino group of (XIII) with propargyl bromide (XIV) and NaH furnishes the title compound