Tert-Butyl nitrite → 12-Chloro-9-trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513633Notes

Reaction equation

HRID 513633 reaction equation
N[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([Cl:26])=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)(=[O:14])=[O:13].N(OC(C)(C)C)=O>CC(O)=O>[Cl:26][C:19]1[CH:18]=[C:17]2[C:16](=[C:25]3[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]3)[NH:15][S:12](=[O:13])(=[O:14])[C:3]1[C:2]2=[CH:7][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 681830122-Amino-N-(5-chloroquinolin-8-yl)-4-trifluoromethyl-benzenesulfonamide2×

Product 1

HCID 6016455012-Chloro-9-trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 33%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-N-(5-chloro-quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamide (Intermediate 302) (350 mg, 0.87 mmol), t-butyl nitrite (0.16 ml, 1.30 mmol) and AcOH (3.5 ml) gave the title compound (110 mg, 33%) after purification by column chromatography with DCM/MeOH/NH3 (99:1:2 drops) as the eluent.

Sources & evidence

ORD record
ord-4763f287b6424df598ee2e80db486a85
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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