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

HRID 513611Notes

Reaction equation

HRID 513611 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]([C:22]([F:25])([F:24])[F:23])=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9].CC(O)=O>C1COCC1>[F:25][C:22]([F:24])([F:23])[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:2]2=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 681834522-Amino-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 6016443312-Trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 12.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide (Intermediate 281) (230 mg, 0.63 mmol), t-butyl nitrile (111 mg, 0.94 mmol) and AcOH:THF (2.3 ml: 2.3 ml) gave the title compound (27 mg, 12%) after purification by column chromatography with DCM/MeOH (99.7:0.3) as the eluent.

Sources & evidence

ORD record
ord-52c2a13293694b80a9e1cda2b2c962c8
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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