Tert-Butyl nitrite → 1-Methoxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513806Notes

Reaction equation

N(OC(C)(C)C)=O.N[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:28]=1[N:27]=[CH:26][CH:25]=[C:24]2[O:29][CH3:30])(=[O:17])=[O:16]>CC(O)=O.C1COCC1>[CH3:30][O:29][C:24]1[C:23]2[C:28](=[C:19]3[C:20](=[CH:21][CH:22]=2)[C:11]2[C:10](=[CH:9][CH:14]=[CH:13][CH:12]=2)[S:15](=[O:17])(=[O:16])[NH:18]3)[N:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 5 °C

Procedure

t-Butyl nitrite (120 μl, 1.1 mmol) added was added to a solution of 2-amino-N-(4-methoxy-quinolin-8-yl)benzenesulfonamide 571 (254 mg, 0.77 mmol) in AcOH/THF (1:1; 10 ml) at 0° C. and the mixture was stirred at 5° C. for 2 h. The crude residue was purified by column chromatography with DCM/MeOH (99:1) as the eluent followed by preparative HPLC (acidic conditions 1) to give the title compound (16 mg, 6%).

Workup

customThe crude residue was purified by column chromatography with DCM/MeOH (99:1) as the eluent

Sources & evidence

ORD record: ord-91ea41c0ac4d48c6a43e16d3a76060ab
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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