HCID 69697293, compound → HCID 10142347, compound

HRID 412592Notes

Reaction equation

HRID 412592 reaction equation
[ClH:1].Cl.C([O:5][C:6]([C:8]1([CH2:20][O:21][C:22]2[C:31]([Cl:32])=[C:30]3[C:25]([CH:26]=[CH:27][C:28]([C:33](=[NH:35])[NH2:34])=[CH:29]3)=[CH:24][CH:23]=2)[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])C>Cl>[ClH:32].[ClH:1].[C:33]([C:28]1[CH:27]=[CH:26][C:25]2[C:30](=[C:31]([Cl:32])[C:22]([O:21][CH2:20][C:8]3([C:6]([OH:7])=[O:5])[CH2:9][CH2:10][N:11]([C:14]4[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=4)[CH2:12][CH2:13]3)=[CH:23][CH:24]=2)[CH:29]=1)(=[NH:34])[NH2:35]

Participants

3

Reactant 1

HCID 69697293HCID 69697293, compound

Product 1

HCID 10142347HCID 10142347, compoundYield 132.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-(2-amidino-8-chloronaphthalen-7-yloxymethyl)-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester dihydrochloride (78 mg) in conc. hydrochloric acid was stirred at 50° C.-100° C. for 3 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was separated by HPLC (0.05% aqueous trifluoroacetic acid:methanol=1:1). The obtained residue was treated with hydrogen chloride-ethanol and dried under reduced pressure to give the title compound (49 mg).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe obtained residue was separated by HPLC (0.05% aqueous trifluoroacetic acid:methanol=1:1)
  4. additionThe obtained residue was treated with hydrogen chloride-ethanol
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-d0bb90e8a4ee4972b905d3ee714a4f3b
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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