Hydrochloric Acid → HCID 22502496, compound

HRID 1006985Notes

Reaction equation

HRID 1006985 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]([S:25]([CH2:28][CH2:29]OCC4C=CC=CC=4)(=[O:27])=[O:26])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[ClH:38].[CH3:39][OH:40]>[Pd]>[ClH:38].[ClH:38].[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]([S:25]([CH2:28][CH2:29][CH2:39][OH:40])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 22503382HCID 22503382, compound

Product 1

HCID 22502496HCID 22502496, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

The resulting 1-(4-ethylpiperazin-1-yl)-3-[4-(2-benzyloxyethyl)sulfonylphenyl]isoquinoline (2.56 g) was converted into a hydrochloride in a conventional manner. The resulting hydrochloride was then dissolved in methanol (50 ml), followed by the addition of 10% palladium/carbon catalyst (0.07 g), and the catalytic reduction was conducted at atmospheric pressure overnight. The 10% palladium/carbon catalyst (0.05 g) was additionally added thereto, and the catalytic reduction was conducted at atmospheric pressure for 1 day. The catalyst was filtered off, while the solvent was evaporated. Water was added to the resulting residue, followed by the addition of a 1N aqueous solution of sodium hydroxide to adjust to pH 8, and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol system), to give 1.23 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. additionWater was added to the resulting residue
  5. additionfollowed by the addition of a 1N aqueous solution of sodium hydroxide
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated
  10. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol system)

Sources & evidence

ORD record
ord-632ee077d2e640c6a1380eeeb04e850b
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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