Hydrochloric Acid → 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-isopropoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane

HRID 55329Notes

Reaction equation

HRID 55329 reaction equation
[Na].[C:2]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]3[N:27]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[C:26]4[CH:36]=[CH:37][CH:38]=[CH:39][C:25]=4[N:24]=3)[CH2:18][CH2:17][CH2:16]2)=[CH:9][CH:8]=1)([OH:4])=[O:3].Cl.[CH:41](O)([CH3:43])[CH3:42]>>[F:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][N:27]2[C:26]3[CH:36]=[CH:37][CH:38]=[CH:39][C:25]=3[N:24]=[C:23]2[N:19]2[CH2:20][CH2:21][CH2:22][N:15]([CH2:14][CH2:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][C:2]([O:4][CH:41]([CH3:43])[CH3:42])=[O:3])=[CH:12][CH:11]=3)[CH2:16][CH2:17][CH2:18]2)=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 67714921HCID 67714921, compound

Product 1

HCID 199575331-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-isopropoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane

Procedure

A solution of 5-[2-[4-(2-carboxyethyl)phenyl]ethyl]-1-[1(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane sodium salt (163 mg) in an isopropanol solution saturated with HCl was refluxed for 4 hours. The solvent was removed under reduced pressure, and the residue was dissolved in methylene chloride (20 ml). The solution was washed with a saturated aqueous NaHCO3 solution and brine. The organic layer was dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on a silica gel column using a mixture of methylene chloride, diethyl ether and methanol (1:1:0.25) as eluent to give 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-isopropoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane (123mg) as a colorless oily liquid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride (20 ml)
  3. washThe solution was washed with a saturated aqueous NaHCO3 solution and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by medium pressure liquid column chromatography on a silica gel column
  7. additiona mixture of methylene chloride, diethyl ether and methanol (1:1:0.25) as eluent

Sources & evidence

ORD record
ord-e19420a5ad094f6d927838ce25ff1919
Source dataset
uspto-grants-1997_04
Patent number
US05624948

Reaction notes

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