Hydrogen Bromide → 2-Amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrile
Reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2OC)=[C:4]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1.Br.[OH-:24].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[N:3]=[C:4]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[C:5]([C:10]2[CH:15]=[CH:14][C:13](=[O:24])[NH:12][CH:11]=2)=[CH:6][C:7]=1[C:8]#[N:9]Participants
Procedure
A solution of 2-amino-6-(2-furyl)-5-(4-methoxy-3-pyridyl)-3-pyridinecarbonitrile (1.0 g, 3.42 mmol) in acetic acid (6 ml)-conc. hydrobromic acid (10 ml) was stirred at 100° C. for 1.5 hours. After cooling as it was, the reaction solution was adjusted to pH 12 to 13 with 5 N sodium hydroxide and washed with ethyl acetate. The organic layer was extracted with 1 N sodium hydroxide (×2), and then the combined aqueous layer was neutralized with 5 N hydrochloric acid. The resulting solid was collected by filtration, to give the title compound (760 mg) as yellow crude crystals. After suspending the product in methanol, 4 N HCl/ethyl acetate was added thereto to dissolved and it subjected to silica gel column chromatography (elution solvent; dichloromethane, dichloromethane:methanol=40:1, 20:1, 10:1). The resulting crude objective compound was suspended in water, and then neutralized with 5 N sodium hydroxide. The solid was collected by filtration and washed with water, to give the title compound (486 mg, 51%) as a yellow solid.
Workup
- temperatureAfter cooling as it
- washwashed with ethyl acetate
- extractionThe organic layer was extracted with 1 N sodium hydroxide (×2)
- filtrationThe resulting solid was collected by filtration
Sources & evidence
- ORD record
- ord-f88040ac3a1449548ba41826f0429bd4
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06750232B2
Reaction notes
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