Acetic Acid → 8,12-Dichloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513614Notes

Reaction equation

HRID 513614 reaction equation
N[C:2]1[CH:7]=[C:6]([F:8])[C:5]([Cl:9])=[CH:4][C:3]=1[S:10]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([Cl:24])=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2)(=[O:12])=[O:11].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[Cl:9][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][C:6]=1[F:8])[C:15]1[C:14](=[C:23]3[C:18](=[C:17]([Cl:24])[CH:16]=1)[CH:19]=[CH:20][CH:21]=[N:22]3)[NH:13][S:10]2(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681832612-Amino-5-chloro-N-(5-chloro-quinolin-8-yl)-4-fluoro-benzenesulfonamide2×

Product 1

HCID 601644368,12-Dichloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the similar fashion using route 16 general procedure 61, 2-amino-5-chloro-N-(5-chloro-quinolin-8-yl)-4-fluoro-benzenesulfonamide (Intermediate 284) (150 mg, 0.38 mmol), t-butyl nitrite (0.07 ml, 0.58 mmol) and AcOH:THF (1.5 ml:1.5 ml) gave the title compound (22 mg, 16%) after purification by column chromatography with chloroform/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-f92cbbe8ab194f3c95683568c2ec20f0
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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