Acetic Acid → 3-(Diethylamino)-5-methoxy-1H-indole-2-carboxamide, monohydrochloride

HRID 21592

Reaktionsgleichung

Reaktionsgleichung von HRID 21592
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][C:5]=1[C:15](OCC)=[O:16])[CH3:2].[NH2-:22].[Li+].C(O)(=O)C.[ClH:28]>CCOCC>[ClH:28].[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][C:5]=1[C:15]([NH2:22])=[O:16])[CH3:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 24532Lithium amideHCID 13837937ethyl 3-(diethylamino)-5-methoxy-1H-indole-2-carboxylate

Produkt 1

HCID 1317190223-(Diethylamino)-5-methoxy-1H-indole-2-carboxamide, monohydrochlorideAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Prepared from ethyl 3-(diethylamino)-5-methoxy-1H-indole-2-carboxylate (Unangst PC, et al., J. Heterocyclic Chem. 1987;24:817) and lithium amide by the procedure described in Example 18, with the exception that dilute acetic acid is substituted for 1.0N HCl during the wash of the ethyl acetate extracts. The crude product is purified by flash chromatography (silica gel, 30% ethyl acetate in dichloromethane elution) to give a foam. The foam is dissolved in ether and treated with gaseous HCl to provide the product salt in 36% yield after recrystallization from acetonitrile; mp 244° C.-dec.

Aufarbeitung

  1. washwash of the ethyl acetate
  2. customThe crude product is purified by flash chromatography (silica gel, 30% ethyl acetate in dichloromethane elution)
  3. customto give a foam
  4. customto provide the product salt in 36% yield
  5. customafter recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-37fa8988fca1478b905c4ec599fe19b5
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424329

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