Hydrochloric Acid → HCID 18542609, compound

HRID 1268160Notes

Reaction equation

HRID 1268160 reaction equation
[ClH:1].Cl.[C:3]([C:6]1[CH:7]=[C:8](/[CH:12]=[CH:13]/[CH2:14][N:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[CH:22][CH:21]=2)[C:16](=[O:19])[CH2:17][OH:18])[CH:9]=[CH:10][CH:11]=1)(=[NH:5])[NH2:4].Cl.[C:34](=[NH:39])(OCC)[CH3:35].C(N(CC)CC)C.Cl>CO.O1CCOCC1>[ClH:1].[ClH:1].[C:34]([N:30]1[CH2:29][CH2:28][CH:27]([O:26][C:23]2[CH:22]=[CH:21][C:20]([N:15]([CH2:14]/[CH:13]=[CH:12]/[C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([C:3](=[NH:4])[NH2:5])[CH:7]=3)[C:16](=[O:19])[CH2:17][OH:18])=[CH:25][CH:24]=2)[CH2:32][CH2:31]1)(=[NH:39])[CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 18542634HCID 18542634, compound

Product 1

HCID 18542609HCID 18542609, compoundYield 160.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[4-(piperidin-4-yloxy)phenyl]-2-hydroxyacetamide dihydrochloride (385 mg) in methanol (20 ml) were added ethyl acetimidate hydrochloride (300 mg) and triethylamine (0.56 ml) at room temperature. The resulting mixture was stirred at room temperature for 12 hours. To the reaction mixture was added a 4M solution of hydrogen chloride in dioxane (1 ml) and the solution was concentrated in vacuo. The residue was purified by preparative HPLC (YMC-Pack ODS YMC) using 14% aqueous acetonitrile as an eluant to afford an amorphous solid. To a solution of the solid in methanol (10 ml) was added a 4M solution of hydrogen chloride in dioxane (0.5 ml) and the mixture was concentrated to dryness in vacuo. A solution of the residual solid in water (about 10 ml) was lyophilized to give the title compound (336 mg, yield 80%) as a colorless amorphous solid.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customThe residue was purified by preparative HPLC (YMC-Pack ODS YMC)
  3. customto afford an amorphous solid
  4. concentrationthe mixture was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-b4b7b13632a849118c54db7cbfae3030
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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