Reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:21])=[C:7]([NH:9][C:10]([C:12]2[N:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)=[O:11])[CH:8]=1)#[N:2].[NH2:22][OH:23]>CCO>[OH:23][N:22]=[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:21])=[C:7]([NH:9][C:10]([C:12]2[N:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]3=[N:14][CH:13]=2)=[O:11])[CH:8]=1)[NH2:2]Participants
Conditions
- Temperature
- 50 °C
Procedure
To a stirred and cooled (0° C.) suspension of N-(5-cyano-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (8) (10 g, 36.2 mmol) in EtOH (225 ml) was added NH2OH (6 mL, 50% in water solution). After the addition, the reaction was stirred at room temperature for 2 hours then heated at 50° C. for another 2 hours. After cooling to room temperature, the mixture was stored in the fridge overnight. The resulting precipitate was filtered, washed with cold EtOH and dried under vacuum to afford N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 9.40 (dt, J=6.8, 1.2 Hz, 1H), 8.15 (s, 1H), 7.88 (d, J=2.0 Hz, 1H), 7.79 (dt, J=9.2, 1.2 Hz, 1H), 7.76 (dd, J=8.0, 1.6 Hz, 1H), 7.52 (ddd, J=9.2, 9.2, 1.2 Hz, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.17 (td, J=6.8, 1.2 Hz, 1H), 2.49 (s, 3H). MS m/z 310.1 (M+1)+.
Workup
- temperaturecooled
- additionAfter the addition
- stirringthe reaction was stirred at room temperature for 2 hours
- temperatureAfter cooling to room temperature
- customwas stored in the fridge overnight
- filtrationThe resulting precipitate was filtered
- washwashed with cold EtOH
- customdried under vacuum
Sources & evidence
- ORD record
- ord-ec5d307b2b6a43ea8ab197c5f0ceb1a9
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754071B2
Linked notes
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