HCID 86757686, compound → HCID 9873662, compound

HRID 2270921Notes

Reaction equation

HRID 2270921 reaction equation
[ClH:1].Cl.[C:3]([N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][C:34]([C:40](=[NH:42])[NH2:41])=[CH:35][CH:36]=4)[CH:31]=3)[S:20]([CH2:23][C:24]([O:26]CC)=[O:25])(=[O:22])=[O:21])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)(=[NH:5])[CH3:4]>Cl>[ClH:1].[ClH:1].[C:3]([N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[CH:14]=[CH:15][C:16]([N:19]([CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][C:34]([C:40](=[NH:41])[NH2:42])=[CH:35][CH:36]=4)[CH:31]=3)[S:20]([CH2:23][C:24]([OH:26])=[O:25])(=[O:22])=[O:21])=[CH:17][CH:18]=2)[CH2:8][CH2:7]1)(=[NH:5])[CH3:4]

Participants

3

Reactant 1

HCID 86757686HCID 86757686, compound

Product 1

HCID 9873662HCID 9873662, compoundYield 140.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

450 mg of ethyl [N-[4-(4-acetimidoylhexahydro-1 H-1,4-diazepin-1-yl)phenyl]-N-[(7-amidino-2-naphthyl)-methyl]sulfamoyl]acetate dihydrochloride obtained in Example 22 was dissolved in 8 ml of concentrated hydrochloric acid, and stirred at room temperature for 14 hours. The reaction mixture was evaporated, and the resulting residue was dissolved in 8 ml of concentrated hydrochloric acid, and stirred at room temperature for 4 hours. The reaction mixture was evaporated, and the resulting residue was purified through ODS column chromatography using an eluent solvent of acetonitrile/water (10/90). A small amount of 1 N hydrochloric acid was added to this, which was then freeze-dried to obtain 302 mg of [N-[4-(4-acet-imidoylhexahydro-1H-1,4-diazepin-1-yl)phenyl]-N-[(7-amidino-2-naphthyl)methyl]sulfamoyl]acetic acid dihydro-chloride.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe resulting residue was dissolved in 8 ml of concentrated hydrochloric acid
  3. stirringstirred at room temperature for 4 hours
  4. customThe reaction mixture was evaporated
  5. customthe resulting residue was purified through ODS column chromatography
  6. additionA small amount of 1 N hydrochloric acid was added to this, which
  7. customwas then freeze-dried

Sources & evidence

ORD record
ord-115c109797d54d86b1ebd0a374822c03
Source dataset
uspto-grants-2001_12
Patent number
US06333320B1

Reaction notes

Loading…