Water → 2-chloro-N-(6-methoxy-[1,5]naphthyridin-4-yl)-acetamide

HRID 1640524Notes

Reaction equation

HRID 1640524 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH2:13].CC([O-])(C)C.[K+].[Cl:20][CH2:21][C:22](OCC)=[O:23].O>C1COCC1>[Cl:20][CH2:21][C:22]([NH:13][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[N:4]=2)[N:9]=[CH:8][CH:7]=1)=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 7751Ethyl chloroacetateHCID 114352366-Methoxy-1,5-naphthyridin-4-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 667373372-chloro-N-(6-methoxy-[1,5]naphthyridin-4-yl)-acetamideYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-methoxy-1,5-naphthyridin-4-amine (553 mg, 3.116 mmol) in THF (45 mL) was added t-BuOK (390 mg, 1.1 eq) at 0° C. The resulting brown suspension was stirred at rt for 1.5 h and then added dropwise to a solution of ethyl chloroacetate (0.337 mL, 1 eq) in THF (30 mL) at −5° C. The mixture was allowed to warm to rt and was further stirred for 3 h. Water was added and the solvent was removed under reduced pressure. The resulting precipitate was filtered and further dried at HV to afford the title intermediate as a beige solid (357 mg, 45% yield).

Workup

  1. temperatureto warm to rt
  2. stirringwas further stirred for 3 h
  3. customthe solvent was removed under reduced pressure
  4. filtrationThe resulting precipitate was filtered
  5. customfurther dried at HV

Sources & evidence

ORD record
ord-699dbfc4c5404fc8b9a1ae1bb6fe4f4c
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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