Hydrogen chloride-ethyl acetate → HCID 178459331, compound

HRID 2423257Notes

Reaction equation

HRID 2423257 reaction equation
Cl.C(OCC)(=O)C.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[C:17]([C:36]([C:38]1[CH:43]=[CH:42][N:41]=[C:40]([O:44]C)[CH:39]=1)=[O:37])[C:18]([C:20]1[CH:21]=[C:22]([S:26]([NH:29][C:30](=[NH:35])[C:31]([OH:34])([CH3:33])[CH3:32])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)=[O:19]>CCO.O1CCOCC1>[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[C:17]([C:36](=[O:37])[C:38]1[CH:43]=[CH:42][NH:41][C:40](=[O:44])[CH:39]=1)[C:18]([C:20]1[CH:21]=[C:22]([S:26]([NH:29][C:30](=[NH:35])[C:31]([OH:34])([CH3:32])[CH3:33])(=[O:27])=[O:28])[CH:23]=[CH:24][CH:25]=1)=[O:19]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 178492606HCID 178492606, compound

Product 1

HCID 178459331HCID 178459331, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 22560076Dioxan ethanolSolvent

Procedure

Under ice cooling, 4 N—HCl/ethyl acetate (0.09 mL) was added to an EtOH/dioxane (2/1) mixed solution (4 mL) of N-({3-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(2-methoxypyridin-4-yl)-3-oxopropanoyl]phenyl}sulfonyl)-2-hydroxy-2-methylpropanimidamide (127 mg), followed by stirring for 1 hour. The reaction mixture was concentrated under reduced pressure. An aqueous sodium hydrogencarbonate solution was added to the resulting residue, followed by extraction with ethyl acetate and concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=10/1) to obtain N-({3-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxo-3-(2-oxo-1,2-dihydropyridin-4-yl)propanoyl]phenyl}sulfonyl)-2-hydroxy-2-methylpropanimidamide (18 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionAn aqueous sodium hydrogencarbonate solution was added to the resulting residue
  3. extractionfollowed by extraction with ethyl acetate and concentration under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-5770bebbe14e470c96dfda2b3dee88be
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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