HCID 69946008, compound → HCID 69945427, compound

HRID 362536Notes

Reaction equation

HRID 362536 reaction equation
[ClH:1].Cl.[C:3]([N:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][C:32]([C:38](=[NH:40])[NH2:39])=[CH:33][CH:34]=4)[CH:29]=3)[C:20](=[O:26])[C:21]([O:23]CC)=[O:22])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)(=[NH:5])[CH3:4]>Cl>[ClH:1].[ClH:1].[C:3]([N:6]1[CH2:7][CH2:8][CH:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][C:32]([C:38](=[NH:39])[NH2:40])=[CH:33][CH:34]=4)[CH:29]=3)[C:20](=[O:26])[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)[CH2:10][CH2:11]1)(=[NH:5])[CH3:4]

Participants

3

Reactant 1

HCID 69946008HCID 69946008, compound

Product 1

HCID 69945427HCID 69945427, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ethyl N-[4-[(1-acetoimidoyl-4-piperidyl)oxy]phenyl]-N-[(7-amidino-2-naphthyl)methyl]oxamate obtained in Example 23 (100 mg) was dissolved in 20 ml of concentrated hydrochloric acid and the solution was allowed to stand at 5° C. for 9 days. The reaction solution was evaporated, and the resulting residue was purified by an ODS (YMC-GEL ODS-A 120-230/70) column chromatography using methanol:water (3:97) as the eluent, followed by addition of a small amount of 1N hydrochloric acid and freeze-drying to give 23 mg of N-[4-[(1-acetoimidoyl-4-piperidyl)oxy]phenyl]-N-[(7-amidino-2-naphthyl)methyl]oxamic acid dihydrochloride.

Workup

  1. customThe reaction solution was evaporated
  2. customthe resulting residue was purified by an ODS (YMC-GEL ODS-A 120-230/70) column chromatography
  3. additionfollowed by addition of a small amount of 1N hydrochloric acid
  4. customfreeze-drying

Sources & evidence

ORD record
ord-257844b3f37343d1996a1b03e19804fc
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

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