Hydrochloric Acid → N-(3-{3-[3-(3-bromo-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoyl)-methanesulfonamide

HRID 410376Notes

Reaction equation

HRID 410376 reaction equation
C(OC(=O)[N:7]=[C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=2)[C:11]2[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=2[N:9]1[CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])=[O:36])[CH:30]=1)(C)(C)C.Cl>CO>[Br:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][N:12]1[C:11]2[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=2[N:9]([CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:30]=[C:31]([CH:32]=[CH:33][CH:34]=2)[C:35]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])=[O:36])[C:8]1=[NH:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67422397[1-(3-Bromo-benzyl)-3-[3-(3-methanesulfonylaminocarbonyl-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-ylidene]-carbamic acid tert-butyl ester

Product 1

HCID 46241105N-(3-{3-[3-(3-bromo-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoyl)-methanesulfonamideYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To [1-(3-bromo-benzyl)-3-[3-(3-methanesulfonylaminocarbonyl-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-ylidene]-carbamic acid tert-butyl ester (90 mg, 0.14 mmol) at rt was added HCl in MeOH (5 ml). The reaction was stirred until the consumption of the starting material was observed by TLC. After this time, the mixture was concentrated under reduced pressure and purified by chromatography on basic alumina eluting with 10% MeOH/chloroform to provide N-(3-{3-[3-(3-bromo-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoyl)-methanesulfonamide (27 mg, 35%). HPLC-MS 557, 559 [M+1]+.

Workup

  1. concentrationAfter this time, the mixture was concentrated under reduced pressure
  2. custompurified by chromatography on basic alumina eluting with 10% MeOH/chloroform

Sources & evidence

ORD record
ord-43e71afad5634c3c90534dd291bf4dd2
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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