Sodium hydride → HCID 17794288, compound

HRID 1006933Notes

Reaction equation

HRID 1006933 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]([OH:24])=[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].[H-].[Na+].[H][H].[CH3:29][C:30](C)([O:33][SiH2]C(C)(C)C)CBr.[Cl-].[NH4+]>C(OCC)(=O)C.CN(C)C=O>[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]([O:24][CH2:29][CH2:30][OH:33])=[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

8

Reactant 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 123845823HCID 123845823, compoundHCID 135719052HCID 135719052, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17794288HCID 17794288, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 7-(4-ethylpiperazin-1-yl)-5-(4-hydroxyphenyl)thieno[2,3-c]pyridine (130 mg)/dimethylformamide (10 ml) solution was added 60% sodium hydride (23 mg) at room temperature. After the evolution of hydrogen was ceased, dimethyl-(t-butyl)silyloxyethyl bromide (100 mg) was added thereto, and the mixture was reacted at room temperature for 12 hr. Ethyl acetate and an aqueous solution of ammonium chloride were added to the reaction solution. The organic phase was separated, washed with water, dried and concentrated. To the resulting residue were added ethanol (20 ml) and a 2N aqueous solution of hydrochloric acid (10 ml), and the mixture was reacted at 50° C. for 30 min, followed by the evaporation. The resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, and dried. The solvent was removed, and the resulting residue was purified by NH-silica gel column chromatography (ethyl acetate), to give 73 mg of the title compound as a pale yellow oil.

Workup

  1. customthe mixture was reacted at room temperature for 12 hr
  2. customThe organic phase was separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. additionTo the resulting residue were added ethanol (20 ml)
  7. customa 2N aqueous solution of hydrochloric acid (10 ml), and the mixture was reacted at 50° C. for 30 min
  8. customfollowed by the evaporation
  9. customThe resulting residue was partitioned between ethyl acetate and water
  10. washThe organic layer was washed with water and brine
  11. customdried
  12. customThe solvent was removed
  13. customthe resulting residue was purified by NH-silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-f7c080af8dea49a0905150e9de116cdd
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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