Hydrochloric Acid → HCID 22502488, compound

HRID 1006999Notes

Reaction equation

HRID 1006999 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:38])[N:26]([CH2:28][CH2:29][O:30]CC4C=CC=CC=4)[CH3:27])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].Cl>CO.[Pd]>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:38])[N:26]([CH2:28][CH2:29][OH:30])[CH3:27])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22503385HCID 22503385, compound

Product 1

HCID 22502488HCID 22502488, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Sequentially, the resulting 1-(4-ethylpiperazin-1-yl)-3-{4-(N-(2-benzyloxyethyl)-N-methylcarbamoyl]phenyl}isoquinoline (0.69 g) was converted into a hydrochloride in a conventional manner and then dissolved in methanol (50 ml). To the resulting solution was added 10% palladium/carbon catalyst (0.20 g), and the catalytic reduction was conducted at atmospheric pressure overnight. The catalyst was filtered off, while the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol system), to give 0.41 g of the free compound of the title compound as a pale yellow amorphous.

Workup

  1. customwas conducted at atmospheric pressure overnight
  2. filtrationThe catalyst was filtered off, while the solvent
  3. customwas evaporated
  4. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol system)

Sources & evidence

ORD record
ord-8a1290c409b9413aa775c6582b08af25
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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