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

HRID 374949

Reaction equation

HRID 374949 reaction equation
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.[CH2:35]([N:39]=[C:40]=[O:41])[CH2:36][CH2:37][CH3:38]>C1COCC1>[CH2:35]([NH:39][C:40]([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]([C:40](=[O:41])[NH:39][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:29][CH:28]=3)[S:7][C:6]=2[CH:34]=1)=[O:41])[CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 5035RaloxifeneHCID 8110Butyl isocyanate

Product 1

HCID 19603579[6-(N-(n-butyl)carbamoyl]-2-[4-(N-(n-butyl)carbamoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl] methanoneYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.47 g (9 mmol) of [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone was dissolved in 250 mL of THF and 4 g (40 mmol) of n-butylisocyanate was added. The reaction mixture, at room temperature and under nitrogen, was allowed to react for 72 hours. The reaction mixture had evaporated by the end of this time and the residue was dissolved in a minimal amount of CHCl3. This solution was chromatographed (HPLC) on a silica gel column, eluted with a linear gradient of CHCl3 to CHCl3 --MeOH (19:1) to afford 4.87 g of the title compound as a tan amorphous powder.

Workup

  1. customat room temperature
  2. customto react for 72 hours
  3. customThe reaction mixture had evaporated by the end of this time
  4. dissolutionthe residue was dissolved in a minimal amount of CHCl3
  5. customThis solution was chromatographed (HPLC) on a silica gel column
  6. washeluted with a linear gradient of CHCl3 to CHCl3 --MeOH (19:1)

Sources & evidence

ORD record
ord-e54ac26562684063b81a3f7e7e89e9b9
Source dataset
uspto-grants-1996_01
Patent number
US05482949

Linked notes

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