Ammonium Chloride → 1-(1-Ethylpiperazin-4-yl)-3-[(1-hydroxypropyl)thiazol-5-yl]isoquinoline dihydrochloride

HRID 1006904Notes

Reaction equation

HRID 1006904 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[S:23][C:22]([CH:24]=[O:25])=[N:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[CH2:26]([Mg]Br)[CH3:27].O1CCCC1.[Cl-:35].[NH4+]>O1CCCC1>[ClH:35].[ClH:35].[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[S:23][C:22]([CH:24]([OH:25])[CH2:26][CH3:27])=[N:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 225024911-(1-Ethylpiperazin-4-yl)-3-(2-formylthiazol-5-yl)isoquinolineHCID 178420660HCID 178420660, compound

Product 1

HCID 225034411-(1-Ethylpiperazin-4-yl)-3-[(1-hydroxypropyl)thiazol-5-yl]isoquinoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(1-Ethylpiperazin-4-yl)-3-(2-formylthiazol-5-yl)isoquinoline (205 mg) was dissolved in tetrahydrofuran (2 ml), 1M ethylmagnesium bromide/tetrahydrofuran solution (0.26 ml) was added thereto under ice-cooling. The resulting mixture was stirred overnight. An aqueous solution of saturated ammonium chloride was added to the reaction solution, which was then extracted with ethyl acetate. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (toluene/acetone system). The resulting product was converted into a hydrochloride in a conventional manner, and then solidified by adding ether thereto, to give the hydrochloride of the title compound as a brown amorphous (20 mg, yield; 23%).

Workup

  1. temperatureunder ice-cooling
  2. extractionwas then extracted with ethyl acetate
  3. washThe resulting organic layer was washed with water
  4. dry with materialdried (over MgSO4)
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (toluene/acetone system)
  7. additionby adding ether

Sources & evidence

ORD record
ord-8b00d774dffd4c188f6271add89a546a
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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