Ethyl Acetate → HCID 22503046, compound

HRID 1251281Notes

Reaction equation

HRID 1251281 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, 3.0M 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. temperaturecooling
  2. stirringthe mixture was further stirred for 3 hr
  3. stirringthe mixture was further stirred for 4.5 hr
  4. stirringthe mixture was stirred
  5. customThe organic layer was separated
  6. washit was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system)

Sources & evidence

ORD record
ord-0a52f1d30f9247ed9f0abb5671483de1
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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