Pyridine → HCID 19966002, Verbindung

HRID 977832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 977832
C1(C)C(C)=CC=CC=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]([OH:29])[CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:15][C:14]=1[NH:30][C:31](=[O:47])[CH2:32][CH:33]1[C:46]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[O:40][C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2)([CH3:12])([CH3:11])[CH3:10].[C:48]1(=[O:54])[O:53][C:51](=[O:52])[CH2:50][CH2:49]1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(OCC)C>[C:48]([O:29][CH:21]([CH2:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])=[C:14]([NH:30][C:31](=[O:47])[CH2:32][CH:33]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:39]=3[O:40][C:41]3[C:46]2=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:15]=1)[CH2:22][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1)(=[O:54])[CH2:49][CH2:50][C:51]([OH:53])=[O:52]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 7237O-XyleneHCID 7922Succinic anhydrideHCID 19966195HCID 19966195, Verbindung

Produkt 1

HCID 19966002HCID 19966002, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

5 ml of a xylene solution containing 74 mg (0.14 mmol) of N-[2-t-butyl-5-(4-cyclohexyl-3-hydroxybutyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Example 12), 15 mg (0.15 mmol) of succinic anhydride, 18 mg (0.15 mmol) of 4-(N,N-dimethylamino)pyridine and 112 mg (1.41 mmol) of pyridine were stirred for 9 hours at 125° C. At the end of this time, the reaction mixture was allowed to return to room temperature. The reaction solution was then diluted with diethyl ether, and washed with dilute aqueous hydrochloric acid and then with water. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 20 g of silica gel. Elution using a gradient elution method, with mixtures of methylene chloride and methanol in ratios ranging from 100:5 to 10:1 by volume as the eluent, afforded 73 mg (yield 84%) of the title compound as a foam-like substance.

Aufarbeitung

  1. customto return to room temperature
  2. washwashed with dilute aqueous hydrochloric acid
  3. customThe solvent was then removed by distillation under reduced pressure
  4. washElution
  5. washa gradient elution method

Quellen und Nachweise

ORD-Eintrag
ord-88b91c41fff7456a9e04d4ad6d4ce8ea
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614550

Notizen zur Reaktion

Wird geladen…