Dimethylformamide → HCID 89767904, compound

HRID 591482Notes

Reaction equation

HRID 591482 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[C:10]([SH:16])=[C:11]([C:13]([NH2:15])=[O:14])[S:12][C:8]=2[CH:7]=1.C(=O)([O-])O.[Na+].Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].CN(C=O)C>C1COCC1>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][S:16][C:10]1[C:9]2[CH:17]=[CH:18][C:6]([O:5][CH2:4][C:3]3[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:2]=3[Cl:1])=[CH:7][C:8]=2[S:12][C:11]=1[C:13](=[O:14])[NH2:15])[CH3:35]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 516892Sodium BicarbonateHCID 89767940HCID 89767940, compound

Product 1

HCID 89767904HCID 89767904, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6-((2,4-dichlorobenzyl)oxy)-3-sulfanyl-1-benzothiophene-2-carboxamide (40 mg) in THF (dry) (4.0 mL) were added sodium hydrogen carbonate (13.1 mg) and ethyl 2-bromoacetate (0.017 mL). The mixture was stirred overnight at room temperature. To the mixture was added DMF (1.0 mL) and stirred at room temperature over weekend. The mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (25.2 mg).

Workup

  1. stirringstirred at room temperature over weekend
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layer was washed successively with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-2cb11a3429ed4d32b2dbcfcceb55a06d
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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