Acetic Acid → 11H-12-Thia-1,10,11-triaza-chrysene 12,12-dioxide

HRID 513617

Reaction equation

HRID 513617 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][S:12]([C:15]2[C:20](N)=[CH:19][CH:18]=[CH:17][N:16]=2)(=[O:14])=[O:13])[CH:4]=[CH:3][CH:2]=1.N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[N:16]1[C:15]2[S:12](=[O:14])(=[O:13])[NH:11][C:9]3[C:8](=[CH:7][CH:6]=[C:5]4[C:10]=3[N:1]=[CH:2][CH:3]=[CH:4]4)[C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681831363-Amino-pyridine-2-sulfonic acid quinolin-8-ylamide2×

Product 1

HCID 6818350911H-12-Thia-1,10,11-triaza-chrysene 12,12-dioxideYield 7.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, using 3-amino-pyridine-2-sulfonic acid quinolin-8-ylamide (Intermediate 303) (180 mg, 0.6 mmol), t-butyl nitrite (0.11 ml, 0.9 mmol), AcOH (1.8 ml) and THF(1.8 ml) gave the title compound (12 mg, 7%) after purification with prep HPLC (neutral conditions).

Sources & evidence

ORD record
ord-8af1baa5bee5406a897ccc1e59dbee1f
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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