2-Bromoacetamide → HCID 22269290, compound

HRID 750756Notes

Reaction equation

HRID 750756 reaction equation
N1CCOCC1.[C:7]([Si:11]([CH3:27])([CH3:26])[O:12][CH2:13][CH2:14][CH2:15][C:16]1[C:17]([C:24]#[N:25])=[C:18]([S-:23])[NH:19][C:20](=[O:22])[CH:21]=1)([CH3:10])([CH3:9])[CH3:8].Br[CH2:29][C:30]([NH2:32])=[O:31]>C1COCC1>[C:7]([Si:11]([CH3:27])([CH3:26])[O:12][CH2:13][CH2:14][CH2:15][C:16]1[C:17]([C:24]#[N:25])=[C:18]([S:23][CH2:29][C:30]([NH2:32])=[O:31])[NH:19][C:20](=[O:22])[CH:21]=1)([CH3:8])([CH3:9])[CH3:10]

Participants

4

Reactant 2

HCID 696322-BromoacetamideHCID 22269319HCID 22269319, compound

Product 1

HCID 22269290HCID 22269290, compoundYield 360.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.940 g (2.28 mmol) of the above morpholine salt in THF (15 mL), cooled to 0° C., was added 0.315 g (0.280 mmol) of 2-bromoacetamide as a solid in one portion. The mixture was stirred and allowed to slowly warm to room temperature over a 2 h period during which time salts precipitated from solution. The mixture was filtered through diatomaceous earth to remove solids and the filter pad was washed with EtOAc. The mixture was concentrated under reduced pressure to provide 0.385 g (44%) of 2-{4-[3-(t-butyl-dimethyl-silanyloxy)-propyl]-3-cyano-6-oxo-1,6-dihydro-pyridin-2-ylsulfanyl}-acetamide as an orange foam.

Workup

  1. customprecipitated from solution
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. customto remove solids
  4. washthe filter pad was washed with EtOAc
  5. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-68caa62d36be402e8a0eb654a6425f0d
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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