Acetic Acid → 3-Chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513613Notes

Reaction equation

HRID 513613 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][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([Cl:22])[CH:18]=[CH:17]2)(=[O:10])=[O:9].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]2[C:21]([N:20]=1)=[C:12]1[C:13]([C:4]3[C:3]([S:8](=[O:10])(=[O:9])[NH:11]1)=[CH:2][CH:7]=[CH:6][CH:5]=3)=[CH:14][CH:15]=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 86669761HCID 86669761, compound2×

Product 1

HCID 601644353-Chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-N-(2-chloro-quinolin-8-yl)-benzenesulfonamide (Intermediate 283) (590 mg, 1.77 mmol), t-butyl nitrite (0.32 ml, 2.65 mmol) and AcOH:THF (5.9 ml: 5.9 ml) gave the title compound (80 mg, 16%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-26dabc08a03a4adeb41cb1b0ba82efd6
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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