Hydroxyamine hydrochloride → 3-[3-(7-Hydroxyiminomethylimidazo[1,2-alpha]pyridin-3-yl)phenyl]thiophene-2-carbonitrile
Reaction equation
Cl.[NH2:2][OH:3].[CH:4]([C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:16]=[C:17]([C:21]4[CH:25]=[CH:24][S:23][C:22]=4[C:26]#[N:27])[CH:18]=[CH:19][CH:20]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1)=O>>[OH:3][N:2]=[CH:4][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:16]=[C:17]([C:21]4[CH:25]=[CH:24][S:23][C:22]=4[C:26]#[N:27])[CH:18]=[CH:19][CH:20]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1Participants
3
Procedure
The title compound was prepared in a similar manner to that described in Example 14 using hydroxylamine hydrochloride (57 mg, 0.82 mmol) and 3-[3-(7-formylimidazo[1,2-α]pyridin-3-yl)phenyl]thiophene-2-carbonitrile (90 mg, 0.27 mmol) to afford a white crystalline solid (77 mg, 82%), essentially as a single geometric isomer, m.p. >230° C. 1H NMR (360 MHz, d6-DMSO) δH 7.27 (1H, dd, J 1 and 7), 7.70-7.82 (3H, m), 7.91 (1H, s), 8.03 (1H, s), 8.17 (1H, d, J 1), 7.90-7.95 (1H, m), 8.17 (1H, d, J 5), 8.31 (1H, s), 8.65 (1H, d, J 7), 11.53 (1H, s); m/z (ES+) 345 (M++H).
Sources & evidence
- ORD record
- ord-9a7027391464494f8f5ef2b76a66b210
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06872731B2
Reaction notes
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