Pyridine → 2,6-difluoro-N-[1,8]naphthyridin-2-ylbenzamide

HRID 1054908Notes

Reaction equation

HRID 1054908 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[CH:4]=[CH:3][C:2]=1[NH2:11].N1C=CC=CC=1.[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21](Cl)=[O:22]>ClCCl.C(OCC)(=O)C>[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21]([NH:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[N:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1)=[O:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 874382,6-Difluorobenzoyl chlorideHCID 41730482-Amino-1,8-naphthyridine

Product 1

HCID 900122172,6-difluoro-N-[1,8]naphthyridin-2-ylbenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

[1,8]-Naphthyridin-2-ylamine (85 mg, 0.59 mmol) was dissolved in dichloromethane (2 mL) and pyridine (0.10 mL, 1.2 mmol). 2,6-Difluorobenzoyl chloride (0.068 mL, 0.76 mmol) was then added and the reaction mixture was stirred at room temperature for 30 minutes. Next, the reaction mixture was diluted with ethyl acetate and washed with water followed by brine. The resulting organic solution was purified by column chromatography (EtOAc/hexanes) to give 2,6-difluoro-N-[1,8]naphthyridin-2-ylbenzamide. Yield 35 mg (21%). LCMS (ESI): calc. C15H9F2N3O=285; obs. M+H=286.

Workup

  1. washwashed with water
  2. customThe resulting organic solution was purified by column chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-2727f30b4f2f490690760cf88ef764a1
Source dataset
uspto-grants-2016_07
Patent number
US09394315B2

Reaction notes

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