HCID 14174697, compound → HCID 9822315, compound

HRID 1814736Notes

Reaction equation

HRID 1814736 reaction equation
[C:1]([NH:3][C:4](=[O:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)#[N:2].CC(C)([O-])C.[K+].Br[CH2:20][C:21]([N:23]([CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:24][C:25]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26])=[O:22]>CN(C=O)C>[C:1]([N:3]([CH2:20][C:21](=[O:22])[N:23]([CH2:33][CH:34]([CH3:35])[CH3:36])[CH2:24][C:25]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26])[C:4](=[O:12])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)#[N:2]

Participants

5

Reactant 3

HCID 14174697HCID 14174697, compoundHCID 224987902-bromo-N-isobutyl-N-(2-morpholin-4-yl-2-oxo-ethyl)-acetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 9822315HCID 9822315, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-Cyano-2-phenylacetamide (160 mg, 1.00 mmol) was dissolved in 5 mL of dry DMF. Potassium t-butoxide (112 mg, 1.00 mmol) was added. This mixture was stirred at room temperature for 30 min. The 2-bromo-N-isobutyl-N-(2-morpholin-4-yl-2-oxo-ethyl)-acetamide (321 mg, 1.00 mmol) from above was dissolved in 5 mL of dry DMF and added to the reaction mixture. The reaction mixture was stirred at room temperature for 2 h and then heated at 70° C. for 6 h. Solvent was removed in vacuo and residue was purified by HPLC to give the title compound (87 mg, 22%) as a clear oil.

Workup

  1. additionadded to the reaction mixture
  2. stirringThe reaction mixture was stirred at room temperature for 2 h
  3. temperatureheated at 70° C. for 6 h
  4. customSolvent was removed in vacuo and residue
  5. customwas purified by HPLC

Sources & evidence

ORD record
ord-d914f4b588994df28c99825d039fa813
Source dataset
uspto-grants-2005_04
Patent number
US06878706B1

Reaction notes

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