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

HRID 2176670Notes

Reaction equation

HRID 2176670 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 Cl, 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-d8b163f408924d49a269b1c4d070bf6e
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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