Tert-Butyl nitrite → 9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513598Notes

Reaction equation

N[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][CH:19]=[CH:18]2)(=[O:11])=[O:10].C(ON=O)(C)(C)C>C(O)(=O)C>[F:8][C:6]1[CH:5]=[C:4]2[C:3]([S:9](=[O:11])(=[O:10])[NH:12][C:13]3[C:14]2=[CH:15][CH:16]=[C:17]2[C:22]=3[N:21]=[CH:20][CH:19]=[CH:18]2)=[CH:2][CH:7]=1

Participants

Conditions

Temperature: 10 °C

Procedure

2-Amino-4-fluoro-N-quinolin-8-yl-benzenesulfonamide (Example Compound 31) (315 mg, 0.99 mmol) was suspended in acetic acid (4 ml) and cooled to 10° C. Tert-butylnitrite (177 μl, 1.49 mmol) was added and the reaction was warmed to room temperature over 10 min. The reaction was quenched water (5 ml) and the resulting solution was concentrated in vacuo. The crude residue was dissolved in acetic acid (2 ml) and irradiated at 120° C. for 10 mins in the microwave. After cooling, the reaction was concentrated in vacuo. The crude residue was purified by preparative HPLC (acidic conditions) to give the title compound (7 mg, 2%).

Workup

temperaturethe reaction was warmed to room temperature over 10 min
customThe reaction was quenched water (5 ml)
concentrationthe resulting solution was concentrated in vacuo
dissolutionThe crude residue was dissolved in acetic acid (2 ml)
customirradiated at 120° C. for 10 mins in the microwave
temperatureAfter cooling
concentrationthe reaction was concentrated in vacuo
customThe crude residue was purified by preparative HPLC (acidic conditions)

Sources & evidence

ORD record: ord-8cab3dc6a9a84c729abfa93246cfa1f0
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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