Formic Acid → 3-amino-N-(3-(3-amino-5-methoxyphenylamino)quinoxalin-2-yl)benzenesulfonamide

HRID 237364Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:12][C:13]2[C:14]([NH:23][S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-])=O)[CH:28]=3)(=[O:26])=[O:25])=[N:15][C:16]3[C:21]([N:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:6]=[C:7]([N+:9]([O-])=O)[CH:8]=1.CCO.C(O)=O.C([O-])=O.[K+]>C1COCC1>[NH2:33][C:29]1[CH:28]=[C:27]([S:24]([NH:23][C:14]2[C:13]([NH:12][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([NH2:9])[CH:6]=3)=[N:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)(=[O:26])=[O:25])[CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 60 °C

Procedure

N-(3-(3-Methoxy-5-nitrophenylamino)quinoxalin-2-yl)-3-nitrobenzenesulfonamide (400 mg, 0.81 mmol) was dissolved in 1:1 THF:EtOH (4 mL), to which was added formic acid (938 μl, 2.42 mmol) and potassium formate (203 mg, 2.42 mmol). The system was flushed with nitrogen, and then 10% wt Pd/C (50 mg) was added. The reaction was then heated to 60° C. Once the reaction was determined complete by LC-MS, it was allowed to cool, and DMF was added for solubility. The solution was then filtered through a nylon frit to remove the catalyst. The filtrate was diluted water and the pH adjusted to 7 and extracted with DCM (2×) and EtOAc (2×). All organic layers were combined and evaporated to dryness to give 3-amino-N-(3-(3-amino-5-methoxyphenylamino)quinoxalin-2-yl)benzenesulfonamide (330 mg, 93%). MS (EI) for C21H20N6O3S: 437.06 (MH+)

Workup

customThe system was flushed with nitrogen
addition10% wt Pd/C (50 mg) was added
temperatureto cool
additionDMF was added for solubility
filtrationThe solution was then filtered through a nylon frit
customto remove the catalyst
extractionextracted with DCM (2×) and EtOAc (2×)
customevaporated to dryness

Sources & evidence

ORD record: ord-e97f897284d240df9554462129ef07ab
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642584B2

Reaction notes

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