Tetrahydrofuran → [6-(N-isopropylcarbamoyl)-2[4-(N-isopropylcarbamoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

HRID 325162

Reaction equation

HRID 325162 reaction equation
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(CC)CC)C.[CH:43]([N:46]=[C:47]=[O:48])([CH3:45])[CH3:44].[N-:49]=[C:50]=[O:51].O1C[CH2:55][CH2:54][CH2:53]1>>[CH:43]([NH:46][C:47]([C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)=[CH:17][CH:18]=3)=[O:12])=[C:9]([C:28]3[CH:29]=[CH:30][C:31]([C:50](=[O:51])[NH:49][CH:54]([CH3:55])[CH3:53])=[CH:32][CH:33]=3)[S:8][C:7]=2[CH:35]=1)=[O:48])([CH3:45])[CH3:44]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 54900Raloxifene HydrochlorideHCID 61277Isopropyl isocyanateHCID 105034Isocyanate

Product 1

HCID 22001237[6-(N-isopropylcarbamoyl)-2[4-(N-isopropylcarbamoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

Procedure

4 g (7.85 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 tetrahydrofuran and 3 g (30 mmol) of triethylamine was added. The reaction mixture was stirred for 15 minutes at room temperature and under nitrogen. 2.77 g (32.6 mmol) of isopropylisocyanate was added. After 24 hours, the reaction was checked by thin layer chromatography for completeness and was not complete. An additional 10.8 g (130.4 mmol) of the isocyanate was added and the reaction was allow to continue for another 96 hours. The desired compound was isolated substantially according to the procedures described in Example 19 to afford 4.01 g of the title compound as a tan amorphous powder.

Workup

  1. waitAfter 24 hours
  2. waitto continue for another 96 hours

Sources & evidence

ORD record
ord-fab393552832498bb275b782c941d389
Source dataset
uspto-grants-2001_04
Patent number
US06221838B1

Linked notes

Loading…