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

HRID 513627Notes

Reaction equation

HRID 513627 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]([Cl: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>[Cl: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 681833472-Amino-N-(5-chloro-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 1675994212-Chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 17.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-N-(5-chloro-quinolin-8-yl)-benzenesulfonamide (Intermediate 295) (370 mg, 1.10 mmol), t-butyl nitrite (171 mg, 1.66 mmol), AcOH (3.7 ml) and THF (3.7 ml) gave the title compound (60 mg, 17%) after purification by column chromatography with n-hexane/DCM (1:1) as the eluent.

Sources & evidence

ORD record
ord-6680fc5d143546009c6c215cdbecf736
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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