Acetic Acid → 9-Chloro-12-trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513612Notes

Reaction equation

HRID 513612 reaction equation
N[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([C:23]([F:26])([F:25])[F:24])=[C:17]2[C:22]=1[N:21]=[CH:20][CH:19]=[CH:18]2)(=[O:11])=[O:10].CC(O)=O>C1COCC1>[Cl:8][C:6]1[CH:7]=[C:2]2[C:3]([S:9](=[O:10])(=[O:11])[NH:12][C:13]3[C:14]2=[CH:15][C:16]([C:23]([F:24])([F:26])[F:25])=[C:17]2[C:22]=3[N:21]=[CH:20][CH:19]=[CH:18]2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 681833502-Amino-4-chloro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 601644349-Chloro-12-trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-4-chloro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide (Intermediate 282) (340 mg, 0.85 mmol), t-butyl nitrile (0.15 ml, 1.27 mmol) and AcOH:THF (3.4 ml: 3.4 ml) gave the title compound (28 mg, 9%) after purification by column chromatography with DCM/MeOH (99.5:0.5) as the eluent.

Sources & evidence

ORD record
ord-39e3f6d3038844c89910309cc11ea0a1
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…