Acetic Acid → 12-Fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513623Notes

Reaction equation

HRID 513623 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([F:22])=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[F:22][C:15]1[CH:14]=[C:13]2[C:12](=[C:21]3[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]3)[NH:11][S:8](=[O:10])(=[O:9])[C:3]1[C:4]2=[CH:5][CH:6]=[CH:7][CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681832092-Amino-N-(5-fluoro-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 6016454812-Fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-N-(5-fluoro-quinolin-8-yl)-benzenesulfonamide (Intermediate 291) (350 mg, 1.1 mmol), t-butyl nitrite (0.2 ml, 1.65 mmol), AcOH (3.5 ml) and THF (3.5 ml) gave the title compound (33 mg, 10%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent followed by recrystallisation with DCM/pentane.

Sources & evidence

ORD record
ord-9a05f8abcea34af28c1b478ee5d66303
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…