3-(4-tert-Butylphenoxy)benzaldehyde → {3-[1-Butyl-2-[3-(4-tert-butyl-phenoxy)-phenyl]-6-(3-diethylaminopropoxy)-1H-benzimidazole-4-yloxy]-propyl}diethyl-amine

HRID 17647Notes

Reaction equation

HRID 17647 reaction equation
[C:1]([C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH:13]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:20]([NH:24][C:25]1[CH:31]=[C:30]([O:32][CH2:33][CH2:34][CH2:35][N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])[CH:29]=[C:28]([O:41][CH2:42][CH2:43][CH2:44][N:45]([CH2:48][CH3:49])[CH2:46][CH3:47])[C:26]=1[NH2:27])[CH2:21][CH2:22][CH3:23]>C(O)C>[CH2:20]([N:24]1[C:25]2[CH:31]=[C:30]([O:32][CH2:33][CH2:34][CH2:35][N:36]([CH2:37][CH3:38])[CH2:39][CH3:40])[CH:29]=[C:28]([O:41][CH2:42][CH2:43][CH2:44][N:45]([CH2:48][CH3:49])[CH2:46][CH3:47])[C:26]=2[N:27]=[C:13]1[C:12]1[CH:15]=[CH:16][CH:17]=[C:10]([O:9][C:8]2[CH:18]=[CH:19][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)[CH:11]=1)[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 946533-(4-tert-Butylphenoxy)benzaldehydeHCID 669775442-Butylamino-4,6-di(3-diethylaminopropoxy)aniline

Product 1

HCID 59699062{3-[1-Butyl-2-[3-(4-tert-butyl-phenoxy)-phenyl]-6-(3-diethylaminopropoxy)-1H-benzimidazole-4-yloxy]-propyl}diethyl-amineYield 88.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

{3-[1-Butyl-2-[3-(4-tert-butyl-phenoxy)-phenyl]-6-(3-diethylaminopropoxy)-1H-benzimidazole-4-yloxy]-propyl}diethyl-amine was formed employing 3(4-t-butyl-phenoxy)benzaldehyde (127 mg; 0.50 mmol) and 2-butylamino-4,6-di(3-diethylaminopropoxy)aniline (synthesized via General Procedures J1 and J2 and I) (1.6 mg; 0.25 mmol) in ethanol (1 mL) following General Procedure K. The crude product was purified by silica gel column chromatography using 10% MeOH in DCM with a gradual increment of triethylamine (0.2 to 1.0%) as eluent to afford 145 mg (76%) of {3-[1-Butyl-2-[3-(4-tert-butyl-phenoxy)-phenyl]-6-(3-diethylaminopropoxy)-1H-benzimidazole-4-yloxy]-propyl}diethyl-amine.

Workup

  1. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-18c08847805343cc8d2e84772b8c9310
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Reaction notes

Loading…