Hydrochloric Acid → HCID 18542693, compound

HRID 1268161Notes

Reaction equation

HRID 1268161 reaction equation
[ClH:1].Cl.Cl.[CH2:4]([N:11]([CH2:25]/[CH:26]=[CH:27]/[C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([NH2:33])=[NH:32])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.[C:38](=[NH:43])(OCC)[CH3:39].C(N(CC)CC)C.Cl>CO.O1CCOCC1>[ClH:1].[ClH:1].[ClH:1].[C:38]([N:22]1[CH2:21][CH2:20][CH:19]([O:18][C:15]2[CH:14]=[CH:13][C:12]([N:11]([CH2:25]/[CH:26]=[CH:27]/[C:28]3[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=3)[C:31]([NH2:33])=[NH:32])[CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:17][CH:16]=2)[CH2:24][CH2:23]1)(=[NH:43])[CH3:39]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 18542575HCID 18542575, compound

Product 1

HCID 18542693HCID 18542693, compoundYield 210%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 3-[3-[N-benzyl-N-[4-(piperidin-4-yloxy)phenyl]amino]-1-(E)-propenyl]benzamidine trihydrochloride (335 mg) in methanol (20 ml) were added ethyl acetimidate hydrochloride (230 mg) and triethylamine (0.51 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 (252 mg, yield 70%) 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-8f61814b598d4bc2b8b1bcaf99aad399
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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