Acetic Acid → 8-Fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513629Notes

Reaction equation

HRID 513629 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[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].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[F:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[C:14]1[C:13](=[C:22]3[C:17](=[CH:16][CH:15]=1)[CH:18]=[CH:19][CH:20]=[N:21]3)[NH:12][S:9]2(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681831462-Amino-5-fluoro-N-quinolin-8-yl-benzenesulfonamide2×

Product 1

HCID 248584918-Fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-5-fluoro-N-quinolin-8-yl-benzenesulfonamide (Intermediate 297) (250 mg, 0.78 mmol), t-butyl nitrite (121 mg, 1.18 mmol), AcOH (2.5 ml) and THF (2.5 ml) gave the title compound (21 mg, 8%) after purification by column chromatography (×2) with n-hexane/DCM (50:50) as the eluent followed by recrystallisation.

Sources & evidence

ORD record
ord-0c4feb62758f4f289d930ddab1753b68
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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