Acetic Acid → 9-Chloro-6,6-dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysene-12-carbonitrile

HRID 513615Notes

Reaction equation

HRID 513615 reaction equation
N[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([C:23]#[N:24])=[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>[Cl: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][C:16]([C:23]#[N:24])=[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 681832792-Amino-4-chloro-N-(5-cyano-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 601644389-Chloro-6,6-dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysene-12-carbonitrileYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-4-chloro-N-(5-cyano-quinolin-8-yl)-benzenesulfonamide (Intermediate 286) (100 mg, 0.27 mmol), t-butyl nitrite (0.047 ml, 0.41 mmol) and AcOH: THF (2 ml: 1 ml) gave the title compound (40 mg, 42%) after purification by column chromatography with chloroform/MeOH (99.5:0.5) as the eluent.

Sources & evidence

ORD record
ord-7a0a29bd41a14cbfb4e9dd5b5a267f4a
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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