Raloxifene → [6-[N-(4-Chlorophenyl)carbamoyl]-2-[4-[N-(4chlorophenyl)carbamoyl]phenyl]benzo[b]thien-3-yl][4-[2-(1piperidinyl)ethoxy]-phenyl]methanone

HRID 374947

Reaktionsgleichung

Reaktionsgleichung von HRID 374947
O[C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:14][CH:13]=3)=[O:11])=[C:8]([C:27]3[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=3)[S:7][C:6]=2[CH:34]=1.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([N:42]=[C:43]=[O:44])=[CH:38][CH:37]=1>C1COCC1>[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([NH:42][C:43]([C:2]2[CH:3]=[CH:4][C:5]3[C:9]([C:10]([C:12]4[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][N:21]5[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]5)=[CH:16][CH:17]=4)=[O:11])=[C:8]([C:27]4[CH:28]=[CH:29][C:30]([C:43](=[O:44])[NH:42][C:39]5[CH:40]=[CH:41][C:36]([Cl:35])=[CH:37][CH:38]=5)=[CH:31][CH:32]=4)[S:7][C:6]=3[CH:34]=2)=[O:44])=[CH:38][CH:37]=1

Komponenten

4

Edukt 2

HCID 5035RaloxifeneHCID 76934-Chlorophenyl Isocyanate

Produkt 1

HCID 18357247[6-[N-(4-Chlorophenyl)carbamoyl]-2-[4-[N-(4chlorophenyl)carbamoyl]phenyl]benzo[b]thien-3-yl][4-[2-(1piperidinyl)ethoxy]-phenyl]methanoneAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5.56 g (10.7 mmol) of [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone was dissolved in 200 mL of dry THF and 5.45 g (35.2 mmol) of 4-chlorophenyl isocynate was added. The reaction mixture was stirred at room temperature under an atmosphere of nitrogen. After 18 hours, the solvent was removed by evaporation in vacuo, and redissolved in CHCl3. The CHCl3 solution was cooled to -20° C. for 24 hours and the precipitate formed was filtered off. The remaining solution was chromatographed (Waters Prep 500, HPLC) on a silica gel column, eluted with a linear gradient of CHCl3 ending with CHCl3 --MeOH (19:l)(v/v). The desired fractions were determined by TLC, combined and evaporated to dryness to afford 4.01 g of the title compound as a tan amorphous powder.

Aufarbeitung

  1. customthe solvent was removed by evaporation in vacuo
  2. dissolutionredissolved in CHCl3
  3. temperatureThe CHCl3 solution was cooled to -20° C. for 24 hours
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. customThe remaining solution was chromatographed (Waters Prep 500, HPLC) on a silica gel column
  7. washeluted with a linear gradient of CHCl3 ending with CHCl3
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-64b7dc5b022e42b2a0b91d27cf873558
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05482949

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