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

HRID 325163Notes

Reaction equation

HRID 325163 reaction equation
Cl.O[C:3]1[C:8]([C:9]([C:11]2[C:12]3[CH:26]=[CH:25][CH:24]=[CH:23][C:13]=3[S:14][C:15]=2[C:16]2[CH:21]=[CH:20][C:19](O)=[CH:18][CH:17]=2)=[O:10])=[CH:7][CH:6]=[C:5]([O:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:4]=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]>O1CCCC1>[C:43]1([NH:49][C:50]([C:24]2[CH:25]=[CH:26][C:12]3[C:11]([C:9]([C:8]4[CH:7]=[CH:6][C:5]([O:27][CH2:28][CH2:29][N:30]5[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]5)=[CH:4][CH:3]=4)=[O:10])=[C:15]([C:16]4[CH:17]=[CH:18][C:19]([C:53](=[O:54])[NH:52][C:42]5[CH:41]=[CH:5][CH:4]=[CH:3][CH:8]=5)=[CH:20][CH:21]=4)[S:14][C:13]=3[CH:23]=2)=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 105034IsocyanateHCID 232940886-Hydroxy-[2-(4-hydroxyphenyl)benzo [b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 tetrahydrofuran 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-methanol (19:1). The desired fractions were combined and evaporated to an oil to afford 3.31 g of the title compound.

Workup

  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-methanol (19:1)
  10. customevaporated to an oil

Sources & evidence

ORD record
ord-bbf5b2aa02e64e7d8c4a6f99a91db6c5
Source dataset
uspto-grants-2001_04
Patent number
US06221838B1

Reaction notes

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