Hydrazine hydrate (1:1) → HCID 123633478, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)=O)[C:5](=[O:16])[N:4]2[C:17]3([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[NH:18][C:19](=[O:20])[C:3]=12.O.[NH2:27][NH2:28]>C(O)C.C(O)(=O)C.O>[N:27](=[C:8]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][N:11]=1)[C:6]1[C:5](=[O:16])[N:4]2[C:17]3([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[NH:18][C:19](=[O:20])[C:3]2=[C:2]([CH3:1])[CH:7]=1)[NH2:28]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 8′-methyl-6′-(pyrimidine-4-carbonyl)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (3, 0.7 g, 2.07 mmol) in ethanol (4 mL), acetic acid (4 mL) and water (4 mL) is added hydrazine hydrate (0.13 g, 4.14 mmol). The reaction is stirred at 80° C. overnight. The reaction is cooled to room temperature and concentrated. The crude is resuspended in dichloromethane and is washed with saturated aqueous sodium bicarbonate solution. The organic layer is dried over magnesium sulfate, filtered and concentrated. The crude is purified via column chromatography to afford 6′-(hydrazono(pyrimidin-4-yl)methyl)-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (4).
Workup
- temperatureThe reaction is cooled to room temperature
- concentrationconcentrated
- washis washed with saturated aqueous sodium bicarbonate solution
- dry with materialThe organic layer is dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude is purified via column chromatography
Sources & evidence
- ORD record
- ord-ffd982564d91453287b4b1168cbc188c
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382248B2
Reaction notes
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