Phenyl isocyanate → [6-(N-Phenylcarbamoyl)-2[4-(N-phenylcarbamoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1piperidinyl)ethoxy]phenyl]methanone

HRID 374951

Reaktionsgleichung

Reaktionsgleichung von HRID 374951
Cl.O[C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:28]3[CH:33]=[CH:32][C:31](O)=[CH:30][CH:29]=3)[S:8][C:7]=2[CH:35]=1.C(N([CH2:41][CH3:42])CC)C.[C:43]1([N:49]=[C:50]=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[N-:52]=[C:53]=[O:54]>C1COCC1>[C:43]1([NH:49][C:50]([C:3]2[CH:4]=[CH:5][C:6]3[C:10]([C:11]([C:13]4[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]5[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]5)=[CH:17][CH:18]=4)=[O:12])=[C:9]([C:28]4[CH:29]=[CH:30][C:31]([C:53](=[O:54])[NH:52][C:42]5[CH:41]=[CH:7][CH:35]=[CH:3][CH:4]=5)=[CH:32][CH:33]=4)[S:8][C:7]=3[CH:35]=2)=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Komponenten

6

Edukt 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 54900Raloxifene HydrochlorideHCID 105034Isocyanate

Produkt 1

HCID 22001246[6-(N-Phenylcarbamoyl)-2[4-(N-phenylcarbamoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1piperidinyl)ethoxy]phenyl]methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3 g (5.9 mmol) of [6-hydroxy-2[4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride was suspended in 250 mL of anhydrous THF and 2 g (20 mmol) of triethylamine was added. The reaction mixture was stirred for 15 minutes at room temperature under nitrogen. 15 mL of phenylisocyanate was added and the reaction was allow to continue for 96 hours. An additional 5 mL of isocyanate was added. After a further 48 hours, the reaction mixture was filtered and evaporated to an oil, The oil was triturated with heptane and the liqiud decanted off. The oil was dissolved in chloroform and chromatographed (HPLC) on a silica gel column, eluted with a linear gradient of chloroform to chloroform-MeOH (19:1). The desired fractions were combined and evaporated to an oil to afford 3.31 g of the title compound.

Aufarbeitung

  1. waitto continue for 96 hours
  2. waitAfter a further 48 hours
  3. filtrationthe reaction mixture was filtered
  4. customevaporated to an oil
  5. customThe oil was triturated with heptane
  6. customthe liqiud decanted off
  7. dissolutionThe oil was dissolved in chloroform
  8. customchromatographed (HPLC) on a silica gel column
  9. washeluted with a linear gradient of chloroform to chloroform-MeOH (19:1)
  10. customevaporated to an oil

Quellen und Nachweise

ORD-Eintrag
ord-44262b97a35a49a78d969be9dd6b39dc
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05482949

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