N-Methoxy-N-methylacetamide → HCID 15224432, compound

HRID 991913Notes

Reaction equation

HRID 991913 reaction equation
[CH3:1][C:2]1[N:3]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=1.C([N-]C(C)C)(C)C.[Li+].CON(C)[C:30](=[O:32])[CH3:31]>O1CCCC1>[CH3:17][CH:16]([CH3:18])[CH2:15][N:3]1[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=[C:2]1[CH2:1][C:30](=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 537505N-Methoxy-N-methylacetamideHCID 2724682Lithium diisopropylamideHCID 13958376HCID 13958376, compound

Product 1

HCID 15224432HCID 15224432, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (1 g, 4.2 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL) then cooled to −78° C. A portion of lithium diisopropyl amide (2.8 mL, 4.2 mmol) was added dropwise to the cooled solution. At 10 minutes post addition, N-methoxy-N-methylacetamide (0.45 g, 4.4 mmol), prepared according to the method of T. A. Oster and T. M. Harris, Tetrahedron Letters, 24, 1851 (1983) was added. After 15 minutes the reaction was quenched with water and the resulting precipitate was collected and dried to provide the desired product as a solid. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. customprepared
  2. additionHarris, Tetrahedron Letters, 24, 1851 (1983) was added
  3. customAfter 15 minutes the reaction was quenched with water
  4. customthe resulting precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-dcef6554cd104244b21d3e94507bb4bd
Source dataset
uspto-grants-2002_10
Patent number
US06465654B2

Reaction notes

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