Acetic Acid → 9-Trifluoromethoxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513632Notes

Reaction equation

HRID 513632 reaction equation
N[C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[S:13]([NH:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]=[CH:24][CH:23]=[CH:22]2)(=[O:15])=[O:14].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[F:11][C:9]([F:12])([F:10])[O:8][C:6]1[CH:7]=[C:2]2[C:3]([S:13](=[O:14])(=[O:15])[NH:16][C:17]3[C:18]2=[CH:19][CH:20]=[C:21]2[C:26]=3[N:25]=[CH:24][CH:23]=[CH:22]2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681833742-Amino-N-quinolin-8-yl-4-trifluoromethoxy-benzenesulfonamide2×

Product 1

HCID 601645499-Trifluoromethoxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 8.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-N-quinolin-8-yl-4-trifluoromethoxy-benzenesulfonamide (Intermediate 301) (350 mg, 0.91 mmol), t-butyl nitrite (0.16 ml, 1.37 mmol), AcOH (3.5 ml) and THF (3.5 ml) gave the title compound (27 mg, 8%) after purification by column chromatography with DCM/MeOH (99.8:0.2) as the eluent.

Sources & evidence

ORD record
ord-be8420b7a4fc4463b4fc3cdf2541466f
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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