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 1604488Notes

Reaction equation

HRID 1604488 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-bdb9ea9d6b864b3ca5a12faaeb9929bf
Source dataset
uspto-grants-1999_11
Patent number
US05994371

Reaction notes

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