Acetic Acid → 9-Chloro-1-trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513610Notes

Reaction equation

HRID 513610 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][CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][CH:19]=[C:18]2[C:23]([F:26])([F:25])[F:24])(=[O:11])=[O:10].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[Cl:8][C:6]1[CH:5]=[C:4]2[C:3]([S:9](=[O:10])(=[O:11])[NH:12][C:13]3[C:14]2=[CH:15][CH:16]=[C:17]2[C:22]=3[N:21]=[CH:20][CH:19]=[C:18]2[C:23]([F:26])([F:24])[F:25])=[CH:2][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681830022-Amino-4-chloro-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 601644329-Chloro-1-trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 18.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-4-chloro-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide (Intermediate 280) (340 mg, 0.85 mmol), t-butyl nitrite (0.15 ml, 1.27 mmol), AcOH (4 ml), THF (4 ml) gave the title compound (60 mg, 18%) after purification by column chromatography with DCM/MeOH (98:2) as the eluent.

Sources & evidence

ORD record
ord-9102599ba04649dfab8dfbea375a0175
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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