Ethanimidic acid, ethyl ester, hydrochloride (1:1) → HCID 178493256, compound

HRID 54755

Reaction equation

HRID 54755 reaction equation
Cl.[C:2](=[NH:7])(OCC)[CH3:3].[NH2:8][CH2:9][CH2:10][O:11][CH:12]1[C:18]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=2[N:16]([C:24](=[O:43])[C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:40])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])=[CH:27][C:26]=2[O:41][CH3:42])[CH2:15][CH2:14][CH2:13]1>C(O)C>[ClH:23].[NH:7]=[C:2]([NH:8][CH2:9][CH2:10][O:11][CH:12]1[C:18]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=2[N:16]([C:24](=[O:43])[C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:40])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])=[CH:27][C:26]=2[O:41][CH3:42])[CH2:15][CH2:14][CH2:13]1)[CH3:3]

Participants

4

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)2×HCID 189172105-(2-aminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

Product 1

HCID 178493256HCID 178493256, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.129 g of ethyl acetoimidate hydrochloride was added to 15 ml of a suspension of 0.5 g of 5-(2-amino-ethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine in ethanol with ice-cooling. The mixture was stirred overnight at room temperature. Then, 0.163 g of ethyl acetoimidate hydrochloride was further added. The mixture was stirred at 50° C. for 7 hours and then refluxed for 3 hours. After cooling, the reaction mixture was subjected to filtration to remove insolubles. The filtrate was concentrated. The residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=30/1) to obtain 0.2 g of 5-[2-(1-iminoethyl)aminoethoxy]-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzo-azepine hydrochloride.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at 50° C. for 7 hours
  3. temperaturerefluxed for 3 hours
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was subjected to filtration
  6. customto remove insolubles
  7. concentrationThe filtrate was concentrated
  8. customThe residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=30/1)

Sources & evidence

ORD record
ord-597fef2014da4af3ba5a26c8d03b5e73
Source dataset
uspto-grants-1997_04
Patent number
US05622947

Linked notes

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