Tert-Butyl nitrite → 9-trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513599Notes

Reaction equation

N[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)(=[O:14])=[O:13].C(ON=O)(C)(C)C>C(O)(=O)C.C1COCC1>[F:9][C:8]([F:10])([F:11])[C:6]1[CH:5]=[C:4]2[C:3]([S:12](=[O:14])(=[O:13])[NH:15][C:16]3[C:17]2=[CH:18][CH:19]=[C:20]2[C:25]=3[N:24]=[CH:23][CH:22]=[CH:21]2)=[CH:2][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Amino-N-quinolin-8-yl-4-trifluoromethyl-benzenesulfonamide (Example Compound 35) (50 mg, 0.14 mmol) was dissolved in acetic acid/THF (1:1; 2 ml) and cooled to 0° C. Tert-butylnitrite (16.2 μl, 0.14 mmol) was added and the mixture was stirred for 1 h keeping the temperature between 0° C. -5° C. The reaction was quenched with water (3 ml), while keeping the temperature between 0° C. -5° C., and the organic phase was extracted with EtOAc (10 ml). The combined organic phases were washed with sat. sodium bicarbonate and concentrated in vacuo. The crude residue was purified by column chromatography with DCM as the eluent to give the title compound (11 mg, 23%)

Workup

custombetween 0° C. -5° C
customThe reaction was quenched with water (3 ml)
custombetween 0° C. -5° C.
extractionthe organic phase was extracted with EtOAc (10 ml)
washThe combined organic phases were washed with sat. sodium bicarbonate
concentrationconcentrated in vacuo
customThe crude residue was purified by column chromatography with DCM as the eluent

Sources & evidence

ORD record: ord-ed881e856b9c45f9ad2f3bd945d6a6d8
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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