Hydrochloric Acid → 2,3-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-benzenesulfonamide

HRID 1029138Notes

Reaction equation

HRID 1029138 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[CH:4][CH:3]=1.[Cl:24][C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[S:32](Cl)(=[O:34])=[O:33].CCN(CC)CC.Cl>O1CCOCC1>[Cl:24][C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[S:32]([NH:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[CH:4][CH:3]=1)(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 581683671-(4-Amino-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 442052892,3-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-benzenesulfonamideYield 17.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Compound 137 (50 mg, 0.16 mmol), 2,3-dichloro-benzenesulfonyl chloride (45 mg, 0.18 mmol), and Et3N (0.07 mL, 0.49 mmol) were suspended in dioxane (2 mL), and stirred overnight at 80° C. The reaction mixture was acidified with 1M HCl, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 25 to 100% EtOAc in hexanes to provide 173 (14 mg, 17% yield) as a white solid. LC-MS (M+H=512, obsd.=512).

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with EtOAc
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified via Biotage
  5. washeluting with a gradient of 25 to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-5a82d64b1cd24b8099be0897252ba853
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

Loading…