Acetic Acid → 8-Methyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513628Notes

Reaction equation

HRID 513628 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[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:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[C:14]1[C:13](=[C:22]3[C:17](=[CH:16][CH:15]=1)[CH:18]=[CH:19][CH:20]=[N:21]3)[NH:12][S:9]2(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 68183321HCID 68183321, compound2×

Product 1

HCID 248584898-Methyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 13.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-5-methyl-N-quinolin-8-yl-benzenesulfonamide (Intermediate 296) (160 mg, 0.51 mmol), t-butyl nitrite (80 mg, 0.76 mmol), AcOH (1.6 ml) and THF (1.6 ml) gave the title compound (20 mg, 13%) after purification by column chromatography with n-hexane/DCM (1:1) as the eluent.

Sources & evidence

ORD record
ord-747fd6f87c974eff931f0e441d48c1a9
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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