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

HRID 5744

Reaction equation

HRID 5744 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH:6]=[CH:7][CH2:8][NH:9][CH2:10][CH2:11][NH:12][S:13]([C:16]2[C:17]3[CH:18]=[CH:19][N:20]=[CH:21][C:22]=3[CH:23]=[CH:24][CH:25]=2)(=[O:15])=[O:14])=[CH:4][CH:3]=1.[OH:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][CH2:8][N:9]([CH2:10][CH2:11][NH:12][S:13]([C:16]2[C:17]3[CH:18]=[CH:19][N:20]=[CH:21][C:22]=3[CH:23]=[CH:24][CH:25]=2)(=[O:14])=[O:15])[CH2:33][C:32]2[CH:35]=[CH:36][C:29]([OH:28])=[CH:30][CH:31]=2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 176156N-[2-(4-Chlorocinnamylamino)ethyl]-5-isoquinolinesulfonamideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 53642189N-{2-[4-Chloro-N-(4-hydroxybenzyl) cinnamylamino]ethyl}-5-isoquinolinesulfonamideYield 59.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-ad93cea3c46c4c05874b445fc5c954fd
Source dataset
uspto-grants-1993_09
Patent number
US05245034

Linked notes

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