Hydrochloric Acid → HCID 18542637, compound

HRID 1268162Notes

Reaction equation

HRID 1268162 reaction equation
[ClH:1].Cl.Cl.[NH:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][CH2:18]/[CH:19]=[CH:20]/[C:21]3[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=3)[C:24]([NH2:26])=[NH:25])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1.Cl.[C:31](=[NH:36])(OCC)[CH3:32].C(N(CC)CC)C.Cl>CO.O1CCOCC1>[ClH:1].[ClH:1].[ClH:1].[C:31]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][CH2:18]/[CH:19]=[CH:20]/[C:21]3[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=3)[C:24]([NH2:26])=[NH:25])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=[NH:36])[CH3:32]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 18542677HCID 18542677, compound

Product 1

HCID 18542637HCID 18542637, compoundYield 217.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 3-[3-[N-[4-(piperidin-4-yloxy)phenyl]amino]-1-(E)-propenyl]benzamidine trihydrochloride (345 mg) in methanol (20 ml) were added ethyl acetimidate hydrochloride (185 mg) and triethylamine (0.52 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 30% 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 (272 mg, yield 72%) as a 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-5d9b0f1621aa45af87316a7e361981a9
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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