Formic Acid → N-[2-(N-formyl-p-chlorocinnamylamino)ethyl]-5-isoquinolinesulfonamide

HRID 1090587

Reaktionsgleichung

Reaktionsgleichung von HRID 1090587
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[Cl:11][C:12]1[CH:37]=[CH:36][C:15]([CH:16]=[CH:17][CH2:18][NH:19][CH2:20][CH2:21][NH:22][S:23]([C:26]2[C:27]3[CH:28]=[CH:29][N:30]=[CH:31][C:32]=3[CH:33]=[CH:34][CH:35]=2)(=[O:25])=[O:24])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH:16]=[CH:17][CH2:18][N:19]([CH2:20][CH2:21][NH:22][S:23]([C:26]2[C:27]3[CH:28]=[CH:29][N:30]=[CH:31][C:32]=3[CH:33]=[CH:34][CH:35]=2)(=[O:24])=[O:25])[CH:1]=[O:3])=[CH:36][CH:37]=1

Komponenten

6

Edukt 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 176156N-[2-(4-Chlorocinnamylamino)ethyl]-5-isoquinolinesulfonamide

Produkt 1

HCID 131319N-[2-(N-formyl-p-chlorocinnamylamino)ethyl]-5-isoquinolinesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3 ml of formic acid and 3 ml of acetic anhydride were mixed and stirred at a room temperature, and to the mixture was added 1.41 g of the product of Example 172, and the mixture was stirred for one hour. The reaction mixture was added to 50 ml of ethyl acetate and 30 ml of saturated sodium carbonate aqueous solution with ice, and the mixture was stirred, and after foaming was terminated, the ethyl acetate layer was sequentially washed twice with water and once with a saturated sodium chloride aqueous solution, and dried over magnesium sulfate, filtered and evaporated under a reduced pressure. The resulting residue was purified on a silica gel column (silica gel 60 g, eluant: 2% methanol in chloroform), to obtain 1.49 g of the title compound as a mixture of two isomers (3:2) in a colorless amorphous form.

Aufarbeitung

  1. stirringthe mixture was stirred for one hour
  2. stirringthe mixture was stirred
  3. customafter foaming was terminated
  4. washthe ethyl acetate layer was sequentially washed twice with water and once with a saturated sodium chloride aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under a reduced pressure
  8. customThe resulting residue was purified on a silica gel column (silica gel 60 g, eluant: 2% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-fcc4dd1547eb439795a18f28ed5f4a41
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081246

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