Potassium Carbonate → HCID 59656694, compound

HRID 2054895Notes

Reaction equation

HRID 2054895 reaction equation
[NH2:1][C:2]1[C:3]2[C:13]([S:14][CH3:15])=[CH:12][C:11]([N:16]3[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]3)=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8].[C:23](=[O:26])([O-])[O-:24].[K+].[K+]>CN(C=O)C.CO.O>[C:3]([O:24][C:23](=[O:26])[NH:22][CH:19]1[CH2:18][CH2:17][N:16]([C:11]2[CH:12]=[C:13]([S:14][CH3:15])[C:3]3[C:2]([NH2:1])=[C:6]([C:7](=[O:8])[NH2:9])[S:5][C:4]=3[CH:10]=2)[CH2:21][CH2:20]1)([CH3:13])([CH3:4])[CH3:2]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 11404945HCID 11404945, compound

Product 1

HCID 59656694HCID 59656694, compoundYield 206.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 0.211 g (0.577 mmol) of the above amide in DMF (5 mL) was added 1.6 mL (1.8 mmol) of a 10% solution of 2-thioacetamide in MeOH along with 0.80 g (5.8 mmol) of potassium carbonate. The mixture was heated to 70° C. for 15 h then cooled to room temperature and diluted with H2O which caused a solid to precipitate from solution. The solid was collected by filtration, washed with H2O and dried under vacuum to provide 0.260 g (100%) of [1-(3-amino-2-carbamoyl-4-methylthio-benzo[b]thiophen-6-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester as a yellow solid.

Workup

  1. temperaturethen cooled to room temperature
  2. customto precipitate from solution
  3. filtrationThe solid was collected by filtration
  4. washwashed with H2O
  5. customdried under vacuum

Sources & evidence

ORD record
ord-565ff713c8674fb88beb9d0b2a259776
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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