Hydrogen Peroxide → 1-Methyl-2-[(4-amidinophenyl)sulfonylmethyl]benzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide Hydrochloride

HRID 50332Notes

Reaction equation

HRID 50332 reaction equation
[ClH:1].C(N(CCC(OCC)=O)C(C1C=CC2N(C)C(CSC3C=CC(C(=N)N)=CC=3)=NC=2C=1)=[O:7])CC.OO.Cl.[CH2:39]([N:42]([CH2:67][CH2:68][C:69]([O:71][CH2:72][CH3:73])=[O:70])[C:43]([C:45]1[CH:66]=[CH:65][C:48]2[N:49]([CH3:64])[C:50]([CH2:52][S:53]([C:55]3[CH:60]=[CH:59][C:58]([C:61](=[NH:63])[NH2:62])=[CH:57][CH:56]=3)=[O:54])=[N:51][C:47]=2[CH:46]=1)=[O:44])[CH2:40][CH3:41].C(OCC)(=O)C.C(O)C>C(O)=O>[ClH:1].[CH2:39]([N:42]([CH2:67][CH2:68][C:69]([O:71][CH2:72][CH3:73])=[O:70])[C:43]([C:45]1[CH:66]=[CH:65][C:48]2[N:49]([CH3:64])[C:50]([CH2:52][S:53]([C:55]3[CH:60]=[CH:59][C:58]([C:61](=[NH:62])[NH2:63])=[CH:57][CH:56]=3)(=[O:7])=[O:54])=[N:51][C:47]=2[CH:46]=1)=[O:44])[CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 184124111-methyl-2-[(4-amidinophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide hydrochlorideHCID 184126971-methyl-2-[(4-amidinophenyl)sulfinylmethyl]benzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide hydrochlorideHCID 21584252Ethanol ethylacetate

Product 1

HCID 184126811-Methyl-2-[(4-amidinophenyl)sulfonylmethyl]benzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide HydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 0.40 g (0.70 mmol) of 1-methyl-2-[(4-amidinophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride in 10 mL of formic acid was mixed with 2 mL of 30% hydrogen peroxide solution and the mixture was stirred for 16 hours at room temperature. Then the solvent was distilled off in vacuo, whereupon the desired compound was obtained as a beige solid (contaminated with some 1-methyl-2-[(4-amidinophenyl)sulfinylmethyl]benzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride). Yield: 95% of theory, C25H31N6O5S (513.62); Rf value: 0.50 (silica gel; ethyl acetate/ethanol/1N hydrochloric acid=50:45:5); EKA mass spectrum: (M+H)+=514.

Workup

  1. distillationThen the solvent was distilled off in vacuo, whereupon the desired compound
  2. customwas obtained as a beige solid (

Sources & evidence

ORD record
ord-7b7a88b0e9e9455abf40c2a1f00d5bf4
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

Loading…