Benzenesulfonyl chloride → N-[1,5]Naphthyridin-4-yl-benzenesulfonamide

HRID 513501Notes

Reaction equation

HRID 513501 reaction equation
[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH2:11])=[CH:3][CH:2]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH:11][S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 5893541,5-Naphthyridin-4-amine2×

Product 1

HCID 68183352N-[1,5]Naphthyridin-4-yl-benzenesulfonamideYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

[1,5]Naphthyridin-4-ylamine (Intermediate 486) (60 mg, 0.41 mmol) was added to a suspension of NaH (60% in mineral oil; 25 mg, 0.53 mmol) in THF (2 ml) at 0° C. followed by a solution of benzenesulfonyl chloride (95 mg, 0.53 mmol) in THF (1 ml). The mixture was stirred at room temperature for 12 h. After completion, the reaction was quenched with water (5 ml) and the aqueous phase was extracted with EtOAc (30 ml). The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH (98:2) as the eluent to give the title compound (30 mg, 30%).

Workup

  1. customAfter completion, the reaction was quenched with water (5 ml)
  2. extractionthe aqueous phase was extracted with EtOAc (30 ml)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography with DCM/MeOH (98:2) as the eluent

Sources & evidence

ORD record
ord-c23348d195094824a5494dead84175ca
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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