The reaction of 3-bromopropanol (I) with TBDMS-Cl, DIEA and DMAP in dichloromethane gives the silyl ether (II), which is treated with PPh3 in refluxing acetonitrile yielding the phosphonium salt (III). The Wittig reaction of (III) with 3-cholestanone (IV) by means of BuLi in DME affords 3-[3-(tert-butyldimethylsilyloxy)propylidene]cholestane (V), which is reduced with H2 over PtO2 in ethyl acetate giving 3beta-[3-(tert-butyldimethylsilyloxy)propyl]cholestane (VI). The reaction of (VI) with TBAF in THF gives the 3-hydroxypropyl derivative (VII), which is treated with CBr4 and PPh3 in dichloromethane yielding the 3-bromopropyl derivative (VIII). The reaction of (VIII) with PPh3 in refluxing chlorobenzene affords the phosphonium salt (IX), which is submitted to a Wittig condensation with 5,5'-carbonylbis(3-chloro-2-methoxybenzoic acid methyl ester) (X) by means of NaN(SiMe3)2 in THF giving the expected condensation intermediate (XI). The intermediate 5,5'-carbonylbis(3-chloro-2-methoxybenzoic acid methyl ester) (X) has been obtained as follows: The dimerization of 3-chloro-2-hydroxybenzoic acid (XII) with H2CO and H2SO4 in methanol gives 5,5'-methylenebis(3-chloro-2-hydroxybenzoic acid) (XIII), which is fully methylated with SO4Me2 or CO3Me2 and K2CO3 yielding 5,5'-methylenebis(3-chloro-2-methoxybenzoic acid methyl ester) (XIV). Finally, this compound is oxidized with CrO3 in acetic anhydride to afford the desired intermediate (X).

The demethylation of intermediate (XI) with BBr3 and SMe2 in hot 1,2-dichloroethane gives the phenolic intermediate (cosalane, XV), which is simultaneously alkylated and esterified with 4-(bromomethyl)benzoic acid methyl ester (XVI) by means of K2CO3 in DMF yielding the tetrabenzylated intermediate (XVII). The final hydrolysis of the benzyl ester and methyl ester groups with KCN and K2CO3 in hot ethanol/water affords the target compound.

The reaction of 3-bromopropanol (I) with TBDMS-Cl, DIEA and DMAP in dichloromethane gives the silyl ether (II), which is treated with PPh3 in refluxing acetonitrile yielding the phosphonium salt (III). The Wittig reaction of (III) with 3-cholestanone (IV) by means of BuLi in DME affords 3-[3-(tert-butyldimethylsilyloxy)propylidene]cholestane (V), which is reduced with H2 over PtO2 in ethyl acetate giving 3beta-[3-(tert-butyldimethylsilyloxy)propyl]cholestane (VI). The reaction of (VI) with TBAF in THF gives the 3-hydroxypropyl derivative (VII), which is treated with CBr4 and PPh3 in dichloromethane yielding the 3-bromopropyl derivative (VIII). The reaction of (VIII) with PPh3 in refluxing chlorobenzene affords the phosphonium salt (IX), which is submitted to a Wittig condensation with 5,5'-carbonylbis(3-chloro-2-methoxybenzoic acid methyl ester) (X) by means of NaN(SiMe3)2 in THF giving the expected condensation intermediate (XI). The intermediate 5,5'-carbonylbis(3-chloro-2-methoxybenzoic acid methyl ester) (X) has been obtained as follows: The dimerization of 3-chloro-2-hydroxybenzoic acid (XII) with H2CO and H2SO4 in methanol gives 5,5'-methylenebis(3-chloro-2-hydroxybenzoic acid) (XIII), which is fully methylated with SO4Me2 or CO3Me2 and K2CO3 yielding 5,5'-methylenebis(3-chloro-2-methoxy-benzoic acid methyl ester) (XIV). Finally, this compound is oxidized with CrO3 in acetic anhydride to afford the desired intermediate (X).

The demethylation of intermediate (XI) with BBr3 and SMe2 in hot 1,2-dichloroethane gives the phenolic intermediate (cosalane, XV), which is simultaneously alkylated and esterified with 4-(bromomethyl)benzoic acid methyl ester (XVI) by means of K2CO3 in DMF yielding the tetrabenzylated intermediate (XVII). The hydrolysis of the benzyl ester and methyl ester groups with KCN and K2CO3 in hot ethanol/water affords the intermediate tetracarboxylic acid (XVIII), which is finally converted into the target sodium salt by reaction with Na2CO3 in methanol or ethanol.

The reaction of 3-bromopropanol (I) with TBDMS-Cl, DIEA and DMAP in dichloromethane gives the silyl ether (II), which is treated with PPh3 in refluxing acetonitrile yielding the phosphonium salt (III). The Wittig reaction of (III) with 3-cholestanone (IV) by means of BuLi in DME affords 3-[3-(tert-butyldimethylsilyloxy)propylidene]cholestane (V), which is reduced with H2 over PtO2 in ethyl acetate giving 3beta-[3-(tert-butyldimethylsilyloxy)propyl]cholestane (VI). The reaction of (VI) with TBAF in THF gives the 3-hydroxypropyl derivative (VII), which is treated with CBr4 and PPh3 in dichloromethane yielding the 3-bromopropyl derivative (VIII). The reaction of (VIII) with PPh3 in refluxing chlorobenzene affords the phosphonium salt (IX), which is submitted to a Wittig condensation with 5,5'-carbonylbis(3-chloro-2-methoxybenzoic acid methyl ester) (X) by means of NaN(SiMe3)2 in THF giving the expected condensation intermediate (XI). The intermediate 5,5'-carbonylbis(3-chloro-2-methoxybenzoic acid methyl ester) (X) has been obtained as follows: The dimerization of 3-chloro-2-hydroxybenzoic acid (XII) with H2CO and H2SO4 in methanol gives 5,5'-methylenebis(3-chloro-2-hydroxybenzoic acid) (XIII), which is fully methylated with SO4Me2 or CO3Me2 and K2CO3 yielding 5,5'-methylenebis(3-chloro-2-methoxybenzoic acid methyl ester) (XIV). Finally, this compound is oxidized with CrO3 in acetic anhydride to afford the desired intermediate (X).

The demethylation of intermediate (XI) with BBr3 and SMe2 in hot 1,2-dichloroethane gives the phenolic intermediate (cosalane, XV), which is simultaneously alkylated and esterified with 4-(bromomethyl)benzoic acid methyl ester (XVI) by means of K2CO3 in DMF yielding the tetrabenzylated intermediate (XVII). The final hydrolysis of the benzyl ester and methyl ester groups with KCN and K2CO3 in hot ethanol/water affords the target compound.

The reaction of 3-bromopropanol (I) with TBDMS-Cl, DIEA and DMAP in dichloromethane gives the silyl ether (II), which is treated with PPh3 in refluxing acetonitrile yielding the phosphonium salt (III). The Wittig reaction of (III) with 3-cholestanone (IV) by means of BuLi in DME affords 3-[3-(tert-butyldimethylsilyloxy)propylidene]cholestane (V), which is reduced with H2 over PtO2 in ethyl acetate giving 3beta-[3-(tert-butyldimethylsilyloxy)propyl]cholestane (VI). The reaction of (VI) with TBAF in THF gives the 3-hydroxypropyl derivative (VII), which is treated with CBr4 and PPh3 in dichloromethane yielding the 3-bromopropyl derivative (VIII). The reaction of (VIII) with PPh3 in refluxing chlorobenzene affords the phosphonium salt (IX), which is submitted to a Wittig condensation with 5,5'-carbonylbis(3-chloro-2-methoxybenzoic acid methyl ester) (X) by means of NaN(SiMe3)2 in THF giving the expected condensation intermediate (XI). The intermediate 5,5'-carbonylbis(3-chloro-2-methoxybenzoic acid methyl ester) (X) has been obtained as follows: The dimerization of 3-chloro-2-hydroxybenzoic acid (XII) with H2CO and H2SO4 in methanol gives 5,5'-methylenebis(3-chloro-2-hydroxybenzoic acid) (XIII), which is fully methylated with SO4Me2 or CO3Me2 and K2CO3 yielding 5,5'-methylenebis(3-chloro-2-methoxy-benzoic acid methyl ester) (XIV). Finally, this compound is oxidized with CrO3 in acetic anhydride to afford the desired intermediate (X).

The demethylation of intermediate (XI) with BBr3 and SMe2 in hot 1,2-dichloroethane gives the phenolic intermediate (cosalane, XV), which is simultaneously alkylated and esterified with 4-(bromomethyl)benzoic acid methyl ester (XVI) by means of K2CO3 in DMF yielding the tetrabenzylated intermediate (XVII). The hydrolysis of the benzyl ester and methyl ester groups with KCN and K2CO3 in hot ethanol/water affords the intermediate tetracarboxylic acid (XVIII), which is finally converted into the target sodium salt by reaction with Na2CO3 in methanol or ethanol.

Title compound was obtained by condensation of the 6-aminoquinazoline (I) with acrylic acid in the presence of EDC.

The demethylation of intermediate (XI) with BBr3 and SMe2 in hot 1,2-dichloroethane gives the phenolic intermediate (cosalane, XV), which is simultaneously alkylated and esterified with 4-(bromomethyl)benzoic acid methyl ester (XVI) by means of K2CO3 in DMF yielding the tetrabenzylated intermediate (XVII). The final hydrolysis of the benzyl ester and methyl ester groups with KCN and K2CO3 in hot ethanol/water affords the target compound.

The demethylation of intermediate (XI) with BBr3 and SMe2 in hot 1,2-dichloroethane gives the phenolic intermediate (cosalane, XV), which is simultaneously alkylated and esterified with 4-(bromomethyl)benzoic acid methyl ester (XVI) by means of K2CO3 in DMF yielding the tetrabenzylated intermediate (XVII). The hydrolysis of the benzyl ester and methyl ester groups with KCN and K2CO3 in hot ethanol/water affords the intermediate tetracarboxylic acid (XVIII), which is finally converted into the target sodium salt by reaction with Na2CO3 in methanol or ethanol.