Trifluoromethanesulfonic acid → (6-((Methylsulfonyl)oxy)-2-(4-((methylsulfonyl)oxy)phenyl)benzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)-, hydrochloride

HRID 1649605Notes

Reaction equation

HRID 1649605 reaction equation
[ClH:1].[N:2]1([CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:20][S:21]([O:24][C:25]1[CH:26]=[CH:27][C:28]2[CH:32]=[C:31]([C:33]3[CH:38]=[CH:37][C:36]([O:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:35][CH:34]=3)[S:30][C:29]=2[CH:44]=1)(=[O:23])=[O:22].FC(F)(F)S(O)(=O)=O.C(=O)(O)[O-].[Na+]>CO.ClCCl>[ClH:1].[CH3:20][S:21]([O:24][C:25]1[CH:26]=[CH:27][C:28]2[C:32]([C:15](=[O:17])[C:14]3[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][N:2]4[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]4)=[CH:19][CH:18]=3)=[C:31]([C:33]3[CH:34]=[CH:35][C:36]([O:39][S:40]([CH3:43])(=[O:41])=[O:42])=[CH:37][CH:38]=3)[S:30][C:29]=2[CH:44]=1)(=[O:22])=[O:23]

Participants

7

Reactant 4

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 57438354-(2-Piperidinoethoxy)benzoic acid hydrochlorideHCID 132860414-(6-(Methylsulfonyloxy)benzo(b)thiophen-2-yl)phenyl methanesulfonate

Product 1

HCID 19603580(6-((Methylsulfonyl)oxy)-2-(4-((methylsulfonyl)oxy)phenyl)benzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)-, hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The acid chloride was formed from 2.0 g. of 4-(2-piperidinoethoxy)benzoic acid, hydrochloride, as described in Example 1, and was combined with 2 g. of 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-benzo[b]thiophene in 50 ml. of dichloromethane. A 2.4 g. portion of trifluoromethanesulfonic acid was added, and the mixture was stirred overnight under reflux. The reaction mixture was then poured over ice and sodium bicarbonate solution, and the organic layer was dried over magnesium sulfate and filtered. The filtrate was evaporated under vacuum to a yellow foam, which was treated with excess 3% hydrogen chloride in anhydrous methanol. The mixture was evaporated to dryness under vacuum to obtain a white foam which was dissolved in 18 ml. of boiling methanol. The solution was cooled to obtain 3.1 g. of the desired product, m.p. 128°-130° C., which was identified by nmr analysis.

Workup

  1. temperatureunder reflux
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum to a yellow foam, which
  5. additionwas treated with excess 3% hydrogen chloride in anhydrous methanol
  6. customThe mixture was evaporated to dryness under vacuum
  7. customto obtain a white foam which
  8. dissolutionwas dissolved in 18 ml
  9. temperatureThe solution was cooled
  10. customto obtain 3.1 g

Sources & evidence

ORD record
ord-e24c749255e14ba39c6cc3c27173394f
Source dataset
uspto-grants-1983_11
Patent number
US04418068

Reaction notes

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