Potassium Carbonate → HCID 59656678, compound

HRID 2054893Notes

Reaction equation

HRID 2054893 reaction equation
[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][CH3:16])=[CH:12][C:11]([N:17]3[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]3)=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8].[C:24](=[O:27])([O-])[O-:25].[K+].[K+]>CN(C=O)C.CO.O>[C:3]([O:25][C:24](=[O:27])[NH:23][CH:20]1[CH2:19][CH2:18][N:17]([C:11]2[CH:12]=[C:13]([O:14][CH2:15][CH3:16])[C:3]3[C:2]([NH2:1])=[C:6]([C:7](=[O:8])[NH2:9])[S:5][C:4]=3[CH:10]=2)[CH2:22][CH2:21]1)([CH3:13])([CH3:4])[CH3:2]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 11371055HCID 11371055, compound

Product 1

HCID 59656678HCID 59656678, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.311 g (0.856 mmol) of the above amide in DMF (5 mL) was added 0.91 mL (1.0 mmol) of a 10% solution of 2-thioacetamide in MeOH along with 0.70 g (5.1 mmol) of potassium carbonate. The mixture was heated to 80° C. for 24 h then cooled to room temperature and diluted with H2O. The mixture was washed with CH2Cl2 and the combined organic phase was washed with H2O, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography to provide 0.093 g (25%) of [1-(3-amino-2-carbamoyl-4-ethoxy-benzo[b]thiophen-6-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester as a white powder.

Workup

  1. temperaturethen cooled to room temperature
  2. washThe mixture was washed with CH2Cl2
  3. washthe combined organic phase was washed with H2O
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-e3df9ec8ac5c4a39b1f907641b9e2f23
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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