Hydrochloric Acid → HCID 11237020, compound

HRID 412578Notes

Reaction equation

HRID 412578 reaction equation
[ClH:1].Cl.C[O:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][O:20][C:21]2[CH:30]=[C:29]3[C:24]([CH2:25][CH2:26][N:27]([C:31](=[NH:33])[NH2:32])[CH2:28]3)=[CH:23][CH:22]=2)[CH2:15][CH2:14]1)=[O:6].[OH-].[Na+].Cl>CO>[ClH:1].[ClH:1].[C:31]([N:27]1[CH2:26][CH2:25][C:24]2[C:29](=[CH:30][C:21]([O:20][CH2:19][CH:16]3[CH2:15][CH2:14][N:13]([C:12]4[CH:11]=[CH:10][N:9]=[CH:8][C:7]=4[C:5]([OH:6])=[O:4])[CH2:18][CH2:17]3)=[CH:22][CH:23]=2)[CH2:28]1)(=[NH:32])[NH2:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11329440HCID 11329440, compound

Product 1

HCID 11237020HCID 11237020, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[4-(2-amidino-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridine-3-carboxylic acid methyl ester dihydrochloride (43 mg) in methanol (0.2 ml) was added 1N aqueous sodium hydroxide solution (0.1 ml), and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the reaction mixture was neutralized with 1N-hydrochloric acid and the solvent was evaporated. The obtained residue was purified by reverse phase preparative thin layer chromatography (40% aqueous acetonitrile, 1% trifluoroacetic acid) and the obtained residue was treated with hydrogen chloride-ethanol solution and dried under reduced pressure to give the title compound (15 mg).

Workup

  1. temperatureunder reflux for 3 hours
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. customThe obtained residue was purified by reverse phase preparative thin layer chromatography (40% aqueous acetonitrile, 1% trifluoroacetic acid)
  5. additionthe obtained residue was treated with hydrogen chloride-ethanol solution
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-7e697b7134274247a55a86c740aaf1d2
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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