2-Naphthalenesulfonyl chloride → HCID 58168377, compound

HRID 1029103Notes

Reaction equation

HRID 1029103 reaction equation
N[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[CH:17]1[C:26]2[C:21](=CC=CC=2)[CH:20]=[CH:19][C:18]=1S(Cl)(=O)=O.C([N:34](CC)C(C)C)(C)C.[O:40]1[CH2:45]COCC1>CO>[CH3:45][O:40][C:18]1[CH:19]=[CH:20][C:21]([NH:34][C:11]2[CH:12]=[C:13]3[C:8](=[N:9][CH:10]=2)[NH:7][C:6](=[O:14])[C:5]2[CH:15]=[CH:16][CH:2]=[CH:3][C:4]3=2)=[CH:26][CH:17]=1

Participants

6

Reactant 4

HCID 71252-Naphthalenesulfonyl chlorideHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 581679519-amino-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168377HCID 58168377, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

9-Amino-5H-benzo[c][1,8]naphthyridin-6-one (15 mg, 0.07 mmol), 2-napthylsulfonyl chloride (24 mg, 0.11 mmol), and N,N-diisopropylethylamine (0.04 mL, 0.21 mmol) were suspended in dioxane (2 mL), and stirred overnight at 60° C. The reaction mixture was diluted with MeOH, filtered, and purified via prep-LC-MS to provide 88 (5 mg, 17% yield) as a solid. LC-MS (M+H=402, obsd.=402). 1H NMR (400 MHz, d6-DMSO): δ 11.89 (s, 1H), 11.22 (s, 1H), 8.72 (d, 1H), 8.47 (d, 2H), 8.19 (d, 1H), 8.16 (dd, 1H), 8.12 (dd, 1H), 8.08 (dd, 1H), 7.99 (dd, 1H), 7.78 (dd, 1H), 7.65 (m, 2H), 7.42 (dd, 1H), 7.32 (m, 1H).

Workup

  1. filtrationfiltered
  2. custompurified via prep-LC-MS

Sources & evidence

ORD record
ord-a17e8c82038b4f72aeff4decfd403ac9
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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