Triethylamine → N-(8-Chloro-1,5-naphthyridin-3-yl)-2-methoxyacetamide

HRID 1513813Notes

Reaction equation

HRID 1513813 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([NH2:12])=[CH:7]2.C(N(CC)CC)C.[CH3:20][O:21][CH2:22][C:23](Cl)=[O:24]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([NH:12][C:23](=[O:24])[CH2:22][O:21][CH3:20])=[CH:7]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 576913478-Chloro-1,5-naphthyridin-3-amine

Product 1

HCID 57691266N-(8-Chloro-1,5-naphthyridin-3-yl)-2-methoxyacetamideYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A round bottom flask under nitrogen was charged with 8-chloro-1,5-naphthyridin-3-amine (41 mg, 0.23 mmol), triethylamine (64 μl, 0.46 mmol), and dichloromethane (1 mL). To this was added 2-methoxyacetyl chloride (42 μL, 0.46 mmol) dropwise via syringe and reaction allowed to stir overnight at room temperature. Next day reaction mixture was diluted with dichloromethane and washed with aqueous sodium bicarbonate solution. Layers separated and organic layer dried over sodium sulfate to afford yellow oil. This was purified by ISCO silica gel chromatography (2-5% MeOH/DCM) to afford N-(8-chloro-1,5-naphthyridin-3-yl)-2-methoxyacetamide (43 mg, 75% yield) as light yellow solid. MS[M+H]=251.9. Calc'd for C11H10ClN3O2=251.7.

Workup

  1. customreaction
  2. customNext day reaction mixture
  3. washwashed with aqueous sodium bicarbonate solution
  4. customLayers separated
  5. dry with materialorganic layer dried over sodium sulfate
  6. customto afford yellow oil
  7. customThis was purified by ISCO silica gel chromatography (2-5% MeOH/DCM)

Sources & evidence

ORD record
ord-25541785f5234332b2492fefa0ac56ca
Source dataset
uspto-grants-2012_07
Patent number
US08217177B2

Reaction notes

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