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

HRID 1090588

Reaktionsgleichung

Reaktionsgleichung von HRID 1090588
[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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 53642189N-{2-[4-Chloro-N-(4-hydroxybenzyl) cinnamylamino]ethyl}-5-isoquinolinesulfonamideAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-44a5f1004dfe4239bbc2e049095d5eb3
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081246

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