Tert-Butyl nitrite → 8,9-Dimethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513600Notes

Reaction equation

N[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[S:10]([NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2)(=[O:12])=[O:11].C(ON=O)(C)(C)C>C(O)(=O)C.C1COCC1>[CH3:9][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][C:6]=1[CH3:8])[C:15]1[C:14](=[C:23]3[C:18](=[CH:17][CH:16]=1)[CH:19]=[CH:20][CH:21]=[N:22]3)[NH:13][S:10]2(=[O:12])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Amino-4,5-dimethyl-N-quinolin-8-yl-benzenesulfonamide (Intermediate 164) (100 mg, 0.31 mmol) was suspended in acetic acid: THF (1:1) (2 ml) and cooled to 0° C. Tert-butylnitrite (54 μl, 0.46 mmol) was added and the reaction was slowly warmed to 5° C. over 3 h. The reaction was quenched with water (4 ml) and the resulting solution was concentrated in vacuo. The residue was dissolved in EtOAc (10 ml) and washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM as the eluent to give the title compound (7 mg, 7%).

Workup

temperaturethe reaction was slowly warmed to 5° C. over 3 h
customThe reaction was quenched with water (4 ml)
concentrationthe resulting solution was concentrated in vacuo
dissolutionThe residue was dissolved in EtOAc (10 ml)
washwashed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe crude residue was purified by column chromatography with DCM as the eluent

Sources & evidence

ORD record: ord-5663b15f2b24467392c03ccd691fa12a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

Loading…