Hydrochloric Acid → HCID 18542598, compound

HRID 1268168Notes

Reaction equation

HRID 1268168 reaction equation
[ClH:1].Cl.Cl.[OH:4][CH2:5][CH2:6][N:7]([CH2:21]/[CH:22]=[CH:23]/[C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([NH2:29])=[NH:28])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1.Cl.[C:34](=[NH:39])(OCC)[CH3:35].C(N(CC)CC)C.Cl>CO.O1CCOCC1>[ClH:1].[ClH:1].[ClH:1].[C:34]([N:18]1[CH2:17][CH2:16][CH:15]([O:14][C:11]2[CH:12]=[CH:13][C:8]([N:7]([CH2:21]/[CH:22]=[CH:23]/[C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=3)[C:27]([NH2:29])=[NH:28])[CH2:6][CH2:5][OH:4])=[CH:9][CH:10]=2)[CH2:20][CH2:19]1)(=[NH:39])[CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 18542723HCID 18542723, compound

Product 1

HCID 18542598HCID 18542598, compoundYield 164.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 3-[3-[N-(2-hydroxyethyl)-N-[4-(piperidin-4-yloxy)phenyl]amino]-1-(E)-propenyl]benzamidine trihydrochloride (295 mg) in methanol (20 ml) were added ethyl acetimidate hydrochloride (362 mg) and triethylamine (0.41 ml) at room temperature. The resulting mixture was stirred at room temperature for 2 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 16% 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 (175 mg, yield 55%) as a pale yellow 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-939989eb39e047b18922da3299176a80
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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