Triethylamine → HCID 86757686, compound

HRID 2270920Notes

Reaction equation

HRID 2270920 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:27]3[CH:32]=[CH:31][C:30]([N:33]4[CH2:39][CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)=[CH:29][CH:28]=3)[S:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])(=[O:20])=[O:19])=[CH:13]2)=[CH:8][CH:7]=1)(=[NH:5])[NH2:4].Cl.[C:41](=[NH:46])(OCC)[CH3:42].C(N(CC)CC)C>C(O)C>[ClH:1].[ClH:1].[C:41]([N:36]1[CH2:37][CH2:38][CH2:39][N:33]([C:30]2[CH:31]=[CH:32][C:27]([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)[S:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])(=[O:20])=[O:19])=[CH:28][CH:29]=2)[CH2:34][CH2:35]1)(=[NH:46])[CH3:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 86757688HCID 86757688, compound

Product 1

HCID 86757686HCID 86757686, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

590 mg of ethyl [N-[(7-amidino-2-naphthyl)methyl]-N-[4-(hexahydro-1H-1,4-diazepin-1-yl)phenyl]sulfamoyl]-acetate dihydrochloride obtained in Example 6 was dissolved in 22 ml of ethanol, to which were added 680 mg of ethyl acetimidate hydrochloride and 555 mg of triethylamine, and stirred at room temperature for 15 hours. The reaction mixture was evaporated, and the resulting residue was purified through ODS column chromatography using an eluent solvent of ethanol/water (10/90). A small amount of 1 N hydrochloric acid was added to this, which was then freeze-dried to obtain 118 mg of ethyl [N-[4-(4-acetimidoylhexahydro-1H-1,4-diazepin-1-yl)phenyl]-N-[(7-amidino-2-naphthyl)methyl]-sulfamoyl]acetate dihydrochloride.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe resulting residue was purified through ODS column chromatography
  3. additionA small amount of 1 N hydrochloric acid was added to this, which
  4. customwas then freeze-dried

Sources & evidence

ORD record
ord-f5454bdc9c934d3f8785aa2ee7bb97f1
Source dataset
uspto-grants-2001_12
Patent number
US06333320B1

Reaction notes

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