Sodium Azide → HCID 178457103, compound

HRID 1405324Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:25]#[N:26])[CH:16]=4)[N:11]=3)=[CH:7][C:6]=2[CH:27]=1.[N-:28]=[N+:29]=[N-:30].[Na+]>CS(C)=O.O.[Zn+2].[Br-].[Br-]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12]([N:11]=3)=[CH:13][CH:14]=[C:15]([C:25]3[NH:30][N:29]=[N:28][N:26]=3)[CH:16]=4)=[CH:7][C:6]=2[CH:27]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 2-(5-fluorobenzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrile (150 mg, 0.42 mmol) in DMSO (30 ml) and water (2 ml) was added ZnBr2 (46.9 mg, 0.21 mmol) and NaN3 (81.3 mg, 1.25 mmol), and the resulting mixture was stirred for 48 h at 130° C. The reaction mixture was quenched with water (100 ml) and adjusted to pH 3 with HCl (2N), extracted with ethyl acetate (4×60 ml), and the organic layers combined and concentrated in vacuo to give the residue, which was purified by silica gel column chromatography (12% methanol in dichloromethane) to afford 3-(5-fluorobenzofuran-2-yl)-N-methyl-N-(propan-2-yl)-7-(1H-tetrazol-5-yl)quinoxalin-2-amine as a yellow solid (62.6 mg, 37%).

Workup

customThe reaction mixture was quenched with water (100 ml)
extractionextracted with ethyl acetate (4×60 ml)
concentrationconcentrated in vacuo
customto give the residue, which
customwas purified by silica gel column chromatography (12% methanol in dichloromethane)

Sources & evidence

ORD record: ord-0d8f7141376b4d2d85a34f41c6b13990
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916561B2

Reaction notes

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