4-Hydroxybenzaldehyde → N-{2-[4-Chloro-N-(4-hydroxybenzyl) cinnamylamino]ethyl}-5-isoquinolinesulfonamide

0.2 g of the product of Example 172 and 0.13 g of p-hydroxybenzaldehyde were dissolved in 10 ml of methanol, to the solution were added 60 mg of sodium cyanoborohydride and two drops of acetic acid, and the mixture was stirred for 2 days at a room temperature. The reaction mixture was concentrated under a reduced pressure, and after adding a saturated sodium chloride aqueous solution, extracted three times with 20 ml of ethyl acetate. The extracts were combined, washed with sodium chloride, dried over magnesium sulfate, filtered and concentrated under a reduced pressure. The resulting residue was purified on a silica gel column (silica gel 10 g, eluant: 2% methanol in chloroform), to obtain 150 mg of the title compound in a colorless amorphous form.

1. concentrationThe reaction mixture was concentrated under a reduced pressure
2. additionafter adding a saturated sodium chloride aqueous solution
3. extractionextracted three times with 20 ml of ethyl acetate
4. washwashed with sodium chloride
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under a reduced pressure
8. customThe resulting residue was purified on a silica gel column (silica gel 10 g, eluant: 2% methanol in chloroform)

ORD record

ord-ad93cea3c46c4c05874b445fc5c954fd

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05245034