Acetic Acid → 9-methyl-5H-quinolino[8,7-c][1,2]benzothiazine 6,6-dioxide

HRID 513626Notes

Reaction equation

HRID 513626 reaction equation
N[C:2]1[CH:7]=[C:6]([CH3:8])[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]=[CH:18]2)(=[O:11])=[O:10].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[CH3:8][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][CH:16]=[C:17]2[C:22]=3[N:21]=[CH:20][CH:19]=[CH:18]2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 167599222-Amino-4-methyl-N-quinolin-8-yl-benzenesulfonamide2×

Product 1

HCID 167599259-methyl-5H-quinolino[8,7-c][1,2]benzothiazine 6,6-dioxideYield 5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-4-methyl-N-quinolin-8-yl-benzenesulfonamide (Intermediate 294) (520 mg, 1.67 mmol), t-butyl nitrite (0.29 ml, 2.5 mmol), AcOH (5.2 ml) and THF (5.2 ml) gave the title compound (20 mg, 5%) after purification by column chromatography with DCM/MeOH (99.7:0.3) as the eluent.

Sources & evidence

ORD record
ord-259589e95294477d8b5873548c3cf391
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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