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

HRID 513601Notes

Reaction equation

HRID 513601 reaction equation
N[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[S:10]([NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2)(=[O:12])=[O:11].C(ON=O)(C)(C)C>>[CH3:9][O:8][C:6]1[CH:5]=[C:4]2[C:3]([S:10](=[O:12])(=[O:11])[NH:13][C:14]3[C:15]2=[CH:16][CH:17]=[C:18]2[C:23]=3[N:22]=[CH:21][CH:20]=[CH:19]2)=[CH:2][CH:7]=1

Participants

3

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 167595172-Amino-4-methoxy-N-quinolin-8-yl-benzenesulfonamide2×

Product 1

HCID 167599549-methoxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 12.5%

Procedure

In a similar fashion using route 16 general procedure 36, 2-amino-4-methoxy-N-quinolin-8-yl-benzenesulfonamide (Example Compound 13) (60 mg, 0.18 mmol) and tert-butylnitrite (32 μl, 0.27 mmol) gave the title compound (7 mg, 10%) after purification by column chromatography with DCM as the eluent followed by a further column with heptane/EtOAC (9:1-0:1) gradient elution and then preparative HPLC (acidic conditions).

Sources & evidence

ORD record
ord-fe929f42e6484782b1c0cb2353c7aab7
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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