Hydrochloric Acid → HCID 178457104, compound

HRID 1405314Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([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][CH:8]=2)[CH:3]=[N:2]1.[N:27]([Na])=[N+:28]=[N-:29].Cl>CS(C)=O.O.Br[Zn]Br>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([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:29][N:28]=[N:27][N:26]=3)[CH:16]=4)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 2-(1H-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrile (150 mg, 0.44 mmol) in DMSO (15 ml) was added dibromozinc (50 mg, 0.22 mmol), azidosodium (86 mg, 1.32 mmol), and water (2 ml), and the resulting mixture was stirred overnight at 130° C. in an oil bath. The solution was diluted with water (200 ml) and adjusted to pH 4 with HCl (2N), extracted with ethyl acetate (5×50 ml), dried over anhydrous magnesium, and concentrated in vacuo to give a residue, which was purified by a silica gel column (10% methanol in dichloromethane) to afford 3-(1H-indazol-5-yl)-N-methyl-N-(propan-2-yl)-7-(1H-tetrazol-5-yl)quinoxalin-2-amine as a yellow solid (38.5 mg, 23%).

Workup

extractionextracted with ethyl acetate (5×50 ml)
dry with materialdried over anhydrous magnesium
concentrationconcentrated in vacuo
customto give a residue, which
customwas purified by a silica gel column (10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-861a1c89cc074420a88955b33776b988
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916561B2

Reaction notes

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