Boron trifluoride etherate → HCID 54230505, compound

HRID 1090561Notes

Reaction equation

HRID 1090561 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH:24]([N:38]([CH3:52])[S:39](C2C3C=CN=CC=3C=CC=2)(=[O:41])=[O:40])[CH2:25][N:26]2[CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:28][CH2:27]2)[CH:12]=CC=1OCC1C=CC=CC=1)C1C=CC=CC=1.B(F)(F)F.C([O:59][CH2:60][CH3:61])C.C(=O)(O)[O-].[Na+].[CH2:67](S)[CH2:68]S>>[OH:8][C:9]1[CH:10]=[C:11]([CH2:23][CH:24]([N:38]([CH3:52])[S:39]([C:27]2[C:67]3[C:68](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:24]=[CH:25][N:26]=2)(=[O:41])=[O:40])[CH2:25][N:26]2[CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:28][CH2:27]2)[CH:12]=[CH:61][C:60]=1[OH:59]

Participants

5

Reactant 4

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 516892Sodium BicarbonateHCID 19796321N-{1-[(3,4-Dibenzyloxyphenyl)methyl]-2-(4-phenylpiperazinyl)ethyl}-N-methyl-5-isoquinoline sulfonamide

Product 1

HCID 54230505HCID 54230505, compound

Procedure

310 mg of the amorphous compound obtained in Example 6 was dissolved in 2 ml of 1,2-ethanedithiol, and to the solution were added 1 ml of boron trifluoride/ethyl ether, and after stirring at a room temperature for 18 hours, was added saturated sodium bicarbonate aqueous solution, and the reaction mixture was extracted twice with a mixture of chloroform and methanol (10:1). The extract was dried over magnesium sulfate, and concentrated under a reduced pressure to obtain a residue, which was applied to a silica gel column and eluted with chloroform/methanol (80:1 to 20:1) to obtain 148 mg of the title compound in a colorless amorphous form.

Workup

  1. extractionthe reaction mixture was extracted twice with a mixture of chloroform and methanol (10:1)
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customto obtain a residue, which
  5. washeluted with chloroform/methanol (80:1 to 20:1)

Sources & evidence

ORD record
ord-c5977a9f5ae845c6893ddf24730d6b1c
Source dataset
uspto-grants-1992_01
Patent number
US05081246

Reaction notes

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