Sodium Azide → HCID 60171472, compound

HRID 1405306Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]([CH3:22])[CH:19]([CH3:21])[CH3:20])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:23]#[N:24])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+]>CS(C)=O.O.[Zn+2].[Br-].[Br-]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]([N:18]([CH:19]([CH3:21])[CH3:20])[CH3:22])=[N:16][C:15]3[C:10]([N:9]=2)=[CH:11][CH:12]=[C:13]([C:23]2[N:25]=[N:26][NH:27][N:24]=2)[CH:14]=3)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 2-(4-fluorophenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrile (150 mg, 0.47 mmol) in DMSO (10.0 mL) and water (10.0 mL) was added NaN3 (90 mg, 1.38 mmol) and ZnBr2 (51.9 mg, 0.23 mmol), and the resulting mixture was stirred for 48 h at 130° C. in an oil bath. The reaction mixture was cooled down to room temperature, diluted with water (150 mL), extracted with dichloromethane (4×40 mL), and the organic layers combined, dried over magnesium sulfate, and concentrated in vacuo to give the residue, which was purified via silica gel column chromatography (2% dichloromethane in methanol) to afford 3-(4-fluorophenyl)-N-isopropyl-N-methyl-7-(2H-tetrazol-5-yl)quinoxalin-2-amine as a light yellow solid (60 mg, 35.0%).

Workup

temperatureThe reaction mixture was cooled down to room temperature
extractionextracted with dichloromethane (4×40 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customto give the residue, which
customwas purified via silica gel column chromatography (2% dichloromethane in methanol)

Sources & evidence

ORD record: ord-78f34d02da4e4f368b85cebf4302c0b1
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916561B2

Reaction notes

Loading…