Hydrochloric Acid → HCID 18542611, compound

HRID 1268169Notes

Reaction equation

HRID 1268169 reaction equation
[ClH:1].Cl.Cl.[C:4]([C:7]1[CH:8]=[C:9](/[CH:13]=[CH:14]/[CH2:15][N:16]([CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[CH:19][CH:18]=2)[CH:10]=[CH:11][CH:12]=1)(=[NH:6])[NH2:5].Cl.[C:39](=[NH:44])(OCC)[CH3:40].C(N(CC)CC)C.Cl>C(O)C.O1CCOCC1>[ClH:1].[ClH:1].[ClH:1].[C:39]([N:27]1[CH2:28][CH2:29][CH:24]([O:23][C:20]2[CH:21]=[CH:22][C:17]([N:16]([CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:15]/[CH:14]=[CH:13]/[C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([C:4](=[NH:5])[NH2:6])[CH:8]=3)=[CH:18][CH:19]=2)[CH2:25][CH2:26]1)(=[NH:44])[CH3:40]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 18542794HCID 18542794, compound

Product 1

HCID 18542611HCID 18542611, compoundYield 217.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 4-[N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[4-(piperidin-4-yloxy)phenyl]amino]butyrate trihydrochloride (1378 mg) in ethanol (20 ml) were added ethyl acetimidate hydrochloride (890 mg) and triethylamine (2.01 ml). The resulting mixture was stirred at room temperature for 4 hours. To the reaction mixture was added a 4M solution of hydrogen chloride in dioxane (1 ml) and the mixture was concentrated in vacuo. The residue was purified by preparative HPLC (YMC-Pack ODS YMC) using 25% aqueous acetonitrile as an eluant to afford an amorphous solid. To a solution of the solid in ethanol (20 ml) was added 1M hydrochloric acid (1.0 ml) and the mixture was concentrated to dryness in vacuo. A solution of the residual solid in water (about 20 ml) was lyophilized to give the title compound (1072 mg, yield 73%) as a pale yellow amorphous solid.

Workup

  1. concentrationthe mixture 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-1823a64c45604991abe3a5adc6efc4f6
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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