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

HRID 513821Notes

Reaction equation

HRID 513821 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]([O:26][CH3:27])=[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>C1COCC1>[CH3:27][O: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:14])(=[O:13])[C:3]1[C:4]2=[CH:5][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:7][CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681833652-Amino-N-(5-methoxy-quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamide

Product 1

HCID 6818333612-Methoxy-9-trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 20 general procedure 61, 2-amino-N-(5-methoxy-quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamide 588 (440 mg, 1.1 mmol), t-butyl nitrite (0.2 ml, 1.6 mmol), AcOH (4.4 ml) and THF (4.4 ml) gave the title compound (19 mg, 5%) after preparative HPLC (neutral conditions).

Sources & evidence

ORD record
ord-436317256a5842159390ac5c45d4cbbf
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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