Potassium Acetate → 1-(Methoxymethyl)-2-[(5-methylpyridin-2-yl)amino]-2-oxoethyl acetate

HRID 1098070Notes

Reaction equation

HRID 1098070 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[K+].Br[CH:7]([CH2:18][O:19][CH3:20])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=1)=[O:9]>C(#N)C>[C:1]([O:4][CH:7]([CH2:18][O:19][CH3:20])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=1)=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 574386182-bromo-3-methoxy-N-(5-methylpyridin-2-yl)propanamide

Product 1

HCID 575045701-(Methoxymethyl)-2-[(5-methylpyridin-2-yl)amino]-2-oxoethyl acetateYield 88.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium acetate (2.01 g, 20.50 mmol) was added to a stirred solution of 2-bromo-3-methoxy-N-(5-methylpyridin-2-yl)propanamide (Step 1) (1.40 g, 5.13 mmol) in ACN (20 mL). The reaction mixture was refluxed for 5 hrs. The reaction mixture was filtered and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with DCM/EtOAc:2/1) to give the title compound as a colourless solid (1.15 g), 1H NMR (300 MHz, CDCl3) δ 8.57 (br s, 1H), 8.11 (m, 2H), 7.52 (dd, 1H), 5.44 (dd, 1H), 3.89 (dd, 1H), 3.78 (dd, 1H), 3.39 (s, 3H), 2.30 (s, 3H), 2.25 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hrs
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified with column chromatography (silica gel, eluting with DCM/EtOAc:2/1)

Sources & evidence

ORD record
ord-c360b38560c84d58adfb787f66a5ca31
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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