Potassium Carbonate → HCID 178446108, compound

HRID 896319Notes

Reaction equation

HRID 896319 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][C:18]2[N:22]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]3[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:20]=3[N:19]=2)[C:9]1=[O:34])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:37][OH:38].C([O-])([O-])=O.[K+].[K+]>CCO>[C:1]([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][C:18]2[N:22]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]3[CH:28]=[CH:29][C:30]([C:32](=[NH:33])[NH:37][OH:38])=[CH:31][C:20]=3[N:19]=2)[C:9]1=[O:34])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 20814119{3-[5-Cyano-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 178446108HCID 178446108, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

{3-[5-Cyano-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl ester (1.5 g, 3.17 mmol), hydroxylamine hydrochloride (660 mg, 9.5 mmol) and K2CO3 (657 mg, 4.75 mmol) are dissolved in EtOH (40 ml) and heated to reflux for 12 h. The reaction mixture was cooled and the product was isolated by filtration to give 870 mg (54%) of {3-[5-(N-Hydroxycarbamimidoyl)-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl ester as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 h
  3. temperatureThe reaction mixture was cooled
  4. customthe product was isolated by filtration

Sources & evidence

ORD record
ord-f562815dab1a4d41a7548696e9d5de74
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

Loading…