HCID 18542611, compound → HCID 69624310, compound

HRID 1268170Notes

Reaction equation

HRID 1268170 reaction equation
[ClH:1].Cl.Cl.[C:4]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH2:33][CH2:34][CH2:35][C:36]([O:38]CC)=[O:37])[CH2:21]/[CH:22]=[CH:23]/[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[NH:32])[NH2:31])[CH:25]=3)=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)(=[NH:6])[CH3:5]>Cl.C(#N)C>[ClH:1].[ClH:1].[ClH:1].[C:4]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[CH:16][C:17]([N:20]([CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])[CH2:21]/[CH:22]=[CH:23]/[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[NH:31])[NH2:32])[CH:25]=3)=[CH:18][CH:19]=2)[CH2:9][CH2:8]1)(=[NH:6])[CH3:5]

Participants

4

Reactant 1

HCID 18542611HCID 18542611, compound

Product 1

HCID 69624310HCID 69624310, compoundYield 183%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Ethyl 4-[N-[4-(1-acetimidoylpiperidin-4-yloxy)phenyl]-N-[3-(3-amidinophenyl)-2-(E)-propenyl]amino]butyrate trihydrochloride (572 mg) was dissolved in 2M hydrochloric acid (20 ml) and the mixture was stirred at room temperature for 2 hours and then at 50° C. for 2 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by preparative HPLC (YMC-Pack ODS YMC) using 18% aqueous acetonitrile as an eluant to afford an amorphous solid. To a solution of the solid in 18% aqueous acetonitrile (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 (333 mg, yield 61%) as a pale brown amorphous solid.

Workup

  1. waitat 50° C. for 2 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative HPLC (YMC-Pack ODS YMC)
  5. customto afford an amorphous solid
  6. concentrationthe mixture was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-d80f51c6198c430184b35b00a200491e
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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