Reaction #156189

Reaction equation

Triphenyl phosphine

di-tert-butyl azodicarboxylate

6-hydroxy-2H-isoquinolin-1-one

3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol

hydrogen chloride ethyl acetate

→

title compound

6-{3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propoxy}-2H-isoquinolin-1-one trihydrochloride

Solvents

tetrahydrofuran

ethyl acetate

Conditions

Workup

1. 1
   Othercondensed under reduced pressure
2. 2
   Otherthe residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=1:0→4:1)
3. 3
   Othercondensed under reduced pressure
4. 4
   workup.STIRRINGwas stirred at room temperature for 30 minutes
5. 5
   OtherThe generated insoluble matter was separated by filtration
6. 6
   Otherwas dried

Procedure

Triphenyl phosphine (51 mg) and di-tert-butyl azodicarboxylate (45 mg) were added to a tetrahydrofuran (THF) solution (1.5 ml) of 6-hydroxy-2H-isoquinolin-1-one (29 mg), and 3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol (40 mg). The mixture was stirred overnight. After the reaction mixture was condensed under reduced pressure, the residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=1:0→4:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution (0.06 ml) was added to an ethyl acetate solution of the residue, which was stirred at room temperature for 30 minutes. The generated insoluble matter was separated by filtration, and was dried to produce the title compound (31.4 mg) as a white powder.

Source