4-(Aminosulphonyl)benzeneboronic acid → 4-(6-Oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yl)-benzenesulfonamide

HRID 1029141Notes

Reaction equation

HRID 1029141 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[NH2:17][S:18]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)(=[O:20])=[O:19]>>[O:12]=[C:6]1[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C:3]2[C:8](=[N:9][CH:10]=[CH:11][C:2]=2[C:24]2[CH:25]=[CH:26][C:21]([S:18]([NH2:17])(=[O:20])=[O:19])=[CH:22][CH:23]=2)[NH:7]1

Participants

3

Reactant 2

HCID 223919774-(Aminosulphonyl)benzeneboronic acidHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 581681804-(6-Oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yl)-benzenesulfonamideYield 2%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 171 using Compound 83 (100 mg, 0.43 mmol) and 4-(aminosulphonyl)benzeneboronic acid (174 mg, 0.87 mmol) to provide 177 (2 mg, 2% yield) as a grey solid. LC-MS (M+H=352, obsd.=352).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-436c2cbb1df4453dbd1f9818c87afa0b
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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