Ethyl Acetate → HCID 22503046, compound

HRID 1814600Notes

Reaction equation

HRID 1814600 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:10]=[C:11]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26](=[O:28])[CH3:27])=[CH:20][CH:19]=3)[CH:12]=[C:13]3[CH:17]=[CH:16][S:15][C:14]=23)[CH2:5][CH2:4]1)[CH3:2].[CH3:29][Mg]Br.CCOCC.[Cl-:37].[NH4+].C(OCC)(=O)C>O1CCCC1>[ClH:37].[ClH:37].[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:10]=[C:11]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])([CH3:29])[CH3:27])=[CH:20][CH:19]=3)[CH:12]=[C:13]3[CH:17]=[CH:16][S:15][C:14]=23)[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 22503295HCID 22503295, compoundHCID 178467822HCID 178467822, compound2×

Product 1

HCID 22503046HCID 22503046, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The resulting 7-(4-ethylpiperazin-1-yl)-5-[4-(3-oxobutyl)phenyl]thieno[2,3-c]pyridine (0.23 g) was dissolved in tetrahydrofuran (10 ml), and the resulting mixture was stirred under ice cooling. To the resulting mixture was added 3.0M methylmagnesium bromide/ether solution (0.39 ml), and the mixture was further stirred for 3 hr. Then, 3.0 M methylmagnesium bromide/ether solution (0.39 ml) was further added thereto, and the mixture was further stirred for 4.5 hr. Then, an aqueous solution of saturated ammonium chloride and ethyl acetate were added to the mixture, and the mixture was stirred. The organic layer was separated, and then it was washed with brine and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system), to give 0.10 g of the free compound of the title compound as a colorless viscous oil.

Workup

  1. stirringthe mixture was further stirred for 3 hr
  2. stirringthe mixture was further stirred for 4.5 hr
  3. stirringthe mixture was stirred
  4. customThe organic layer was separated
  5. washit was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system)

Sources & evidence

ORD record
ord-5753ea519a11468690440aab21ec8775
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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