Water → 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 4-[[2-(1-Pyrrolidinyl)ethyl]-amino]phenyl Ketone Trioxalate Hydrate

HRID 1387083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1387083
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[C:16]=3[C:24]([C:26]3[CH:31]=[CH:30][C:29](F)=[CH:28][CH:27]=3)=[O:25])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:33][CH2:34][CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.[C:41](=[O:44])([O-:43])[O-:42].[K+].[K+].[OH2:47]>CN(C=O)C>[OH2:8].[C:24]([OH:25])(=[O:47])[C:41]([OH:43])=[O:44].[C:41]([OH:42])(=[O:44])[C:7]([OH:8])=[O:47].[C:24]([OH:25])(=[O:47])[C:41]([OH:43])=[O:44].[N:36]1([CH2:35][CH2:34][NH:33][C:29]2[CH:30]=[CH:31][C:26]([C:24]([C:16]3[C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[S:19][C:15]=3[C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:10][CH:11]=3)=[O:25])=[CH:27][CH:28]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 13441-PyrrolidineethanamineHCID 11430Potassium CarbonateHCID 107182054-Fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

Produkt 1

HCID 211829432-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 4-[[2-(1-Pyrrolidinyl)ethyl]-amino]phenyl Ketone Trioxalate HydrateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

4-Fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone (Example 145, Part A) (1.1 g; 2.5 mmol) was combined with 1.6 mL (12.3 mmol) of 1-(2-aminoethyl)pyrrolidine and 1.0 g (7.4 mmol) of potassium carbonate in 2 mL of dry DMF. The mixture was heated in an oil bath maintained at 130° C. for 18 h. After cooling to room temperature, the mixture was poured into 150 mL of water and stirred for 0.5 h. The product was isolated by filtration and washed with fresh water. The title compound (0.9 g; 68% yield) was purified by flash chromatography on silica gel, eluting with a gradient of hexanes(75-15%)/Et3N(5%)/THF(20-80%). Conversion to the trioxalate was effected as in Example 137, Part E.

Aufarbeitung

  1. temperatureThe mixture was heated in an oil bath
  2. temperatureAfter cooling to room temperature
  3. customThe product was isolated by filtration
  4. washwashed with fresh water

Quellen und Nachweise

ORD-Eintrag
ord-40d8e26693e3470fb8acb8165a88419f
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265575B1

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