Acetic Acid → 12-Methyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513603Notes

Reaction equation

HRID 513603 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:22])=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9].N(OC(C)(C)C)=O.C(O)(=O)C>C1COCC1>[CH3:22][C:15]1[CH:14]=[C:13]2[C:12](=[C:21]3[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]3)[NH:11][S:8](=[O:10])(=[O:9])[C:3]1[C:4]2=[CH:5][CH:6]=[CH:7][CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681834622-Amino-N-(5-methylquinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 6016409212-Methyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 31, 2-amino-N-(5-methylquinolin-8-yl)-benzenesulfonamide (Intermediate 176) (150 mg, 0.48 mmol), tert-butyl nitrite (0.12 ml, 0.88 mmol), acetic acid (28 μl, 0.48 mmol) and THF (5 ml), at 0° C. for 2 h then at room temperature for 2 h, gave the title compound (50 mg, 53%) after purification by column chromatography using silica basified with TEA with n-hexane/EtOAc (1:1) followed by DCM/MeOH (1:0-199:1) gradient elution.

Workup

  1. waitat room temperature for 2 h

Sources & evidence

ORD record
ord-1c1fc174d81345d082c388dbfb22423b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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