Triethylamine → HCID 69946248, compound

HRID 362535Notes

Reaction equation

HRID 362535 reaction equation
[ClH:1].Cl.[C:3]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH2:16][N:17]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)=[CH:23][CH:22]=3)[C:18](=[O:20])[CH3:19])=[CH:13]2)=[CH:8][CH:7]=1)(=[NH:5])[NH2:4].Cl.[C:35](=[NH:40])(OCC)[CH3:36].C(N(CC)CC)C>C(O)C>[ClH:1].[ClH:1].[C:35]([N:31]1[CH2:30][CH2:29][CH:28]([O:27][C:24]2[CH:25]=[CH:26][C:21]([N:17]([CH2:16][C:12]3[CH:11]=[CH:10][C:9]4[C:14](=[CH:15][C:6]([C:3](=[NH:4])[NH2:5])=[CH:7][CH:8]=4)[CH:13]=3)[C:18](=[O:20])[CH3:19])=[CH:22][CH:23]=2)[CH2:33][CH2:32]1)(=[NH:40])[CH3:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 69945474HCID 69945474, compound

Product 1

HCID 69946248HCID 69946248, compoundYield 197.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-[(7-Amidino-2-naphthyl)methyl]-N-[4-[(4-piperidyl)oxy]phenyl]acetamide dihydrochloride (56 mg) was dissolved in 2 ml of ethanol, 28 mg of ethyl acetoimidate hydrochloride and 36 mg of triethylamine were added to the solution, and the mixture was stirred at room temperature for 2 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 (2:98) as the eluent, followed by addition of a small amount of 1N hydrochloric acid and freeze-drying to give 60 mg of N-[4-[(1-acetoimidoyl-4-piperidyl)oxy]phenyl]-N-[(7-amidino-2-naphthyl)methyl]acetamide 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-0064c5fda7664bcc823e576857380857
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

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