Acetic Acid → 11-Methoxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513602Notes

Reaction equation

HRID 513602 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]=[C:14]([O:22][CH3:23])[CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9].C(O)(=O)C.N(OC(C)(C)C)=O>>[CH3:23][O:22][C:14]1[CH:15]=[C:16]2[C:21]([N:20]=[CH:19][CH:18]=[CH:17]2)=[C:12]2[C:13]=1[C:4]1[C:3]([S:8](=[O:10])(=[O:9])[NH:11]2)=[CH:2][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681834062-Amino-N-(6-methoxyquinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 6016409311-Methoxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 36%

Procedure

In a similar fashion using route 16 general procedure 31, 2-amino-N-(6-methoxyquinolin-8-yl)-benzenesulfonamide (Intermediate 169) (100 mg, 0.30 mmol), acetic acid (0.02 ml, 0.32 mmol) and tert-butyl nitrite (60 mg, 0.61 mmol) gave the title compound (19 mg, 36%) after purification by column chromatography with DCM/n-hexane (9:1-1:0) followed by DCM/MeOH (199:1) gradient elution.

Sources & evidence

ORD record
ord-bb18bbff2e444793a536650c07932f07
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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