合成路线1

The reaction of 4-chlorothieno[3,2-c]pyridine (I) with KOH in phenol at 140 C followed by ammonium acetate at 155 C gives thieno[3,2-c]pyridine-4-amine (II), which is benzoylated with benzoyl anhydride in pyridine yielding the benzamide (III). The formylation of (III) with DMF and LDA, followed by reduction with NaBH4 in methanol/THF affords the hydroxymethyl compound (IV), which is converted into the mesylate (V) with MsCl and TEA in dichloromethane. The reaction of (V) with LiCl in THF provides the chloromethyl compound (VI), which is condensed with the protected aminomalonate (VII) by means of sodium ethoxide in ethanol/dioxane to give the adduct (VIII). The selective decarboxylation and deprotection of (VIII) with HCl in hot acetic acid yields the amino acid (IX), which is esterified with SOCl2 and methyl to the corresponding methyl ester (X). The condensation of (X) with 7-methoxynaphthalen-2-ylsulfonyl chloride (XI) by means of TEA in dichloromethane affords the sulfonamide (XII), which is finally condensed with 4-methylpiperidine (XIII) by means of NaOH and TBTU in DMF. Alternatively, the protection of the amino acid (IX) with Boc2O and TEA in methanol gives the carbamate (XIV), which is condensed with 4-methylpiperidine (XIII) by means of NaOH and TBTU in DMF yielding the piperidide (XV). Finally, this compound is deprotected with TFA and condensed with sulfonyl chloride (XI) and TEA to afford the target compound.