4-Amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid → 4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxamide

HRID 1756819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756819
[NH2:1][C:2]1[C:10]2[CH2:9][CH2:8][O:7][C:6]=2[C:5]([C:11]([OH:13])=O)=[CH:4][C:3]=1[Cl:14].[NH2:15][CH2:16][CH2:17][C:18]12[CH2:25][CH2:24][CH2:23][N:22]1[CH2:21][CH2:20][CH2:19]2>O1CCCC1>[NH2:1][C:2]1[C:10]2[CH2:9][CH2:8][O:7][C:6]=2[C:5]([C:11]([NH:15][CH2:16][CH2:17][C:18]23[CH2:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH2:25]3)=[O:13])=[CH:4][C:3]=1[Cl:14]

Komponenten

4

Edukt 2

HCID 106324014-Amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acidHCID 107969772-(Hexahydro-1H-pyrrolizin-7a-yl)ethanamine

Produkt 1

HCID 105217924-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxamideAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Into an agitating solution of 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid (3.21 g) in absolute tetrahydrofuran (50 ml), was added little by little 1,1-carbonylimidazole (2.43 g) and after lapsed 1 hour, a solution of 5-(2-aminoethyl)-1-azabicyclo[3.3.0]octane (2.31 g) in absolute tetrahydrofuran (2 ml) was added therein to reflux for 1 hour. After cooled, the solvent was distilled out in vacuo, a residue was dissolved into chloroform, washed with saturated sodium hydrogen carbonate solution and then water, and thereafter, the solvent was distilled out in vacuo. The resulting residue was refined by alumina column chromatography (developing solvent: chloroform) to afford 4.1 g of the titled compound.

Aufarbeitung

  1. temperatureto reflux for 1 hour
  2. temperatureAfter cooled
  3. distillationthe solvent was distilled out in vacuo
  4. dissolutiona residue was dissolved into chloroform
  5. washwashed with saturated sodium hydrogen carbonate solution
  6. distillationwater, and thereafter, the solvent was distilled out in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-78f3a3584fb04af6bdf6cb37fd3abae8
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05442077

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