E-(3-{4-[1-(4-{2-[4-(3-Dipropylaminopropoxy)phenyl]benzoimidazol-1-yl}but-2-enyl)-1H-benzoimidazol-2-yl]phenoxy}propyl)dipropylamine → (3-{4-[1-(4-{2-[4-(3-Dipropylaminopropoxy)phenyl]benzoimidazol-1-yl}butyl)-1H-benzoimidazol-2-yl]phenoxy}propyl)dipropylamine

HRID 36342Notes

Reaction equation

HRID 36342 reaction equation
[CH2:1]([N:4]([CH2:54][CH2:55][CH3:56])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH2:20]/[CH:21]=[CH:22]/[CH2:23][N:24]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[N:26]=[C:25]3[C:33]3[CH:49]=[CH:48][C:36]([O:37][CH2:38][CH2:39][CH2:40][N:41]([CH2:45][CH2:46][CH3:47])[CH2:42][CH2:43][CH3:44])=[CH:35][CH:34]=3)[C:18]3[CH:50]=[CH:51][CH:52]=[CH:53][C:17]=3[N:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH3:3]>CO.[Pd]>[NH3:4].[CH2:54]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH2:20][CH2:21][CH2:22][CH2:23][N:24]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[N:26]=[C:25]3[C:33]3[CH:34]=[CH:35][C:36]([O:37][CH2:38][CH2:39][CH2:40][N:41]([CH2:42][CH2:43][CH3:44])[CH2:45][CH2:46][CH3:47])=[CH:48][CH:49]=3)[C:18]3[CH:50]=[CH:51][CH:52]=[CH:53][C:17]=3[N:16]=2)=[CH:11][CH:10]=1)[CH2:55][CH3:56]

Participants

5

Reactant 1

HCID 10395316E-(3-{4-[1-(4-{2-[4-(3-Dipropylaminopropoxy)phenyl]benzoimidazol-1-yl}but-2-enyl)-1H-benzoimidazol-2-yl]phenoxy}propyl)dipropylamine

Product 2

HCID 222AmmoniaHCID 15291584(3-{4-[1-(4-{2-[4-(3-Dipropylaminopropoxy)phenyl]benzoimidazol-1-yl}butyl)-1H-benzoimidazol-2-yl]phenoxy}propyl)dipropylamineYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

E-(3-{4-[1-(4-{2-[4-(3-Dipropylaminopropoxy)phenyl]benzoimidazol-1-yl}but-2-enyl)-1H-benzoimidazol-2-yl]phenoxy}propyl)dipropylamine (Example 2) (100 mg) is hydrogenated at 50 pounds per square inch (psi) in methanol (20 mL) with 20% palladium on carbon (10 mg) for 6 hours. The mixture is filtered and evaporated to leave a yellow solid. The solid is purified by MPLC on silica gel eluting with 200:8:1 dichloromethane:ethanol:0.880 aqueous ammonia to give 49 mg of the title compound as a white solid; mp 141°-143° C.

Workup

  1. filtrationThe mixture is filtered
  2. customevaporated
  3. customto leave a yellow solid
  4. customThe solid is purified by MPLC on silica gel eluting with 200:8:1 dichloromethane

Sources & evidence

ORD record
ord-6bbb39b4e082438ba6d449ed8bdca679
Source dataset
uspto-grants-1995_05
Patent number
US05414010

Reaction notes

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