HCID 12052636, compound → 5-(tert-Butyldimethylsilyloxy)-1-(3-methoxy-4-methoxycarbonylbenzyl)-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-benzimidazole

HRID 1264072Notes

Reaction equation

HRID 1264072 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([O:27][CH3:28])[CH:18]=2)=[C:11]([NH:29][C:30](=O)[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][N:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)=[CH:33][CH:32]=2)[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CC1C=CC=CC=1C>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]2[N:15]([CH2:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([O:27][CH3:28])[CH:18]=3)[C:30]([C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][N:40]4[CH2:41][CH2:42][CH2:43][CH2:44]4)=[CH:33][CH:32]=3)=[N:29][C:11]=2[CH:10]=1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 12052636HCID 12052636, compound

Product 1

HCID 120526225-(tert-Butyldimethylsilyloxy)-1-(3-methoxy-4-methoxycarbonylbenzyl)-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-benzimidazoleYield 82%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To the above amide (Example 1, Part E; 3.95, 6.23 mmol) was added o-xylene (50 mL) and the mixture heated at reflux overnight. After concentrating under reduced pressure the resulting residue was purified by flash chromatography (SiO2, 5% MeOH in CHCl3 with 1% Et3N v/v added); yielding 3.1 g (82%) of the desired product.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux overnight
  3. concentrationAfter concentrating under reduced pressure the resulting residue
  4. customwas purified by flash chromatography (SiO2, 5% MeOH in CHCl3 with 1% Et3N
  5. additionv/v added)

Sources & evidence

ORD record
ord-17e0be0bfea84aa6b601d2c6ed6230a1
Source dataset
uspto-grants-2003_04
Patent number
US06541499B1

Reaction notes

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