Hydrochloric Acid → HCID 18542583, compound

HRID 1268165Notes

Reaction equation

HRID 1268165 reaction equation
[ClH:1].Cl.Cl.[CH2:4]([N:6]([CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([NH2:28])=[NH:27])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:9][CH:8]=1)[CH3:5].Cl.[C:33](=[NH:38])(OCC)[CH3:34].C(N(CC)CC)C.Cl>CO.O1CCOCC1>[ClH:1].[ClH:1].[ClH:1].[C:33]([N:17]1[CH2:16][CH2:15][CH:14]([O:13][C:10]2[CH:11]=[CH:12][C:7]([N:6]([CH2:20]/[CH:21]=[CH:22]/[C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26]([NH2:28])=[NH:27])[CH2:4][CH3:5])=[CH:8][CH:9]=2)[CH2:19][CH2:18]1)(=[NH:38])[CH3:34]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 18542835HCID 18542835, compound

Product 1

HCID 18542583HCID 18542583, compoundYield 189.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 3-[3-[N-ethyl-N-[4-(piperidin-4-yloxy)phenyl]amino]-1-(E)-propenyl]benzamidine trihydrochloride (420 mg) in methanol (20 ml) were added ethyl acetimidate hydrochloride (319 mg) and triethylamine (0.72 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 20% 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 (287 mg, yield 63%) 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-2fbdeb62338b442a8a43b0d6ad862a0d
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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