Hydroxylamine → 4-(6-Bromo-1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)-furazan-3-amine

HRID 1986369Notes

Reaction equation

[Br:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([C:17](=[N:20][OH:21])[C:18]#[N:19])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C([N:24](CC)CC)C.NO.O>C1COCC1>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([C:17]3[C:18]([NH2:24])=[N:19][O:21][N:20]=3)[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

The product from Step 6 (2.7 g, 7.93 mmol) in THF (5 mL) and triethylamine (1.1 mL, 7.93 mmol) was treated with a 50% solution of hydroxylamine in water (0.24 mL, 7.93 mmol). The mixture was heated at 120° C. in a sealed tube for 10 h and the reaction allowed to cool to room temperature. The resulting precipitate was filtered and dried in vacuo to afford the title compound (1.7 g, 60%). MS (ES+) m/e 357/359 [M+H]+.

Workup

temperatureto cool to room temperature
filtrationThe resulting precipitate was filtered
customdried in vacuo

Sources & evidence

ORD record: ord-fb2d6472c7dd4149b089675262f2d8b4
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547779B2

Reaction notes

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