Iopamidol, SQ-13396, Iopamyron, Niopam

碘帕醇Chemical Name: N,N'-Bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[2(S)-hydroxypropionamido]-2,4,6-triiodoisophthalamide; N,N'-Bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[2(S)-hydroxypropionamido]-2,4,6-triiodobenzene-1,3-dicarboxamide
CAS No. 60166-93-0
项目整合开发状态: Launched
项目研究机构: Bracco (Originator), Nihon Schering (Not Determined)
合成路线:It can be prepared in three related ways:1) The reaction of 5-amino-2,4,6-triiodoisophthalic acid (I) with refluxing SOCl2 gives 5-amino-2,4,6-triiodoisophthaloyl chloride (II),which is condensed with 2-acetoxypropionyl chloride (III) in dimethylacetamide to afford 5-(2-acetoxypropionylamido)-2,4,6-triiodoisophthaloyl chloride (IV).The condensation of (IV) with 1,3-dihydroxyisopropylamine (V) by means of tributylamine in dimethylacetamide yields 5-(2-acetoxypropionylamido)-2,4,6-triiodoisophthalic acid di-(1,3-dihydroxyisopropylamide) (VI),which is finally hydrolyzed with NaOH in water.

合成路线:2) The reaction of 5-amino-2,4,6-triiodoisophthalic acid (I) with refluxing SOCl2 gives 5-amino-2,4,6-triiodoisophthaloyl chloride (II),which is condensed with 1,3-dihydroxyisopropylamine (V) by means of tributylamine in dimethylacetamide to give 5-amino-2,4,6-triiodoisophthalic acid di-(1,3-dihydroxyisopropylamide) (VII),which is then condensed with 2-acetoxypropionyl chloride (III) to give 5-(2-acetoxypropionylamido)-2,4,6-triiodoisophthalic acid di-(1,3-dihydroxyisopropylamide) (VI),which is finally hydrolyzed with NaOH in water.

合成路线:3) Dimehtyl 5-nitroisophthalate (VIII) is treated with dihydroisopropylamine (V) at 140-50 C to yield 5-nitroisophthalic acid di-(1,3-dihydroxyisopropylamide) (IX),which is hydrogenated with H2 over Pd/C in ethanol giving 5-aminoisophthalic acid di-(1,3-dihydroxyisopropylamide) (X).The reaction of (X) with KICl2 in acidic water at 50-60 C affords 5-amino-2,4,6-triiodoisophthalic acid di-(1,3-dihydroxyisopropylamide) (VII),which is finally acylated with 2-acetoxypropionyl chloride (III) to afford 5-(2-acetoxypropionylamido)-2,4,6-triiodoisophthalic acid di-(1,3-dihydroxyisopropylamide) (VI),which is finally hydrolyzed with NaOH in water