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

HRID 1070334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070334
O.[C:2]([OH:7])(=[O:6])[C:3]([OH:5])=[O:4].[C:8]([OH:13])(=[O:12])[C:9]([OH:11])=[O:10].[N:14]1([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[S:32][C:31]4[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=4[C:29]=3[C:37]([C:39]3[CH:44]=[CH:43][C:42](OCCCCN4CCCC4)=[CH:41][CH:40]=3)=[O:38])=[CH:24][CH:23]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1.[NH2:55][CH2:56][CH2:57][N:58]1[CH2:62][CH2:61][CH2:60][CH2:59]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[OH2:4].[C:8]([OH:13])(=[O:12])[C:9]([OH:11])=[O:10].[C:2]([OH:7])(=[O:6])[C:3]([OH:5])=[O:4].[C:2]([OH:7])(=[O:6])[C:3]([OH:5])=[O:4].[N:58]1([CH2:57][CH2:56][NH:55][C:42]2[CH:41]=[CH:40][C:39]([C:37]([C:29]3[C:30]4[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=4[S:32][C:28]=3[C:25]3[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH2:19][N:14]4[CH2:15][CH2:16][CH2:17][CH2:18]4)=[CH:23][CH:24]=3)=[O:38])=[CH:44][CH:43]=2)[CH2:62][CH2:61][CH2:60][CH2:59]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 13441-PyrrolidineethanamineHCID 11430Potassium CarbonateHCID 211827494-[4-(1-Pyrrolidinyl)butoxy]phenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone Dioxalate Hydrate

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 130,5 %

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-bb570f7e48d247598da13b3dd544e2bf
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251921B1

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