Ammonium Acetate → HCID 21913531, compound
Reaction equation
C([O-])(=O)C.[NH4+:5].[CH2:6]([C:10]1[N:11]([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:12]2[C:17]([CH3:18])=[C:16]([CH3:19])[N:15]=[C:14](OC3C=CC=CC=3)[C:13]=2[N:27]=1)[CH2:7][CH2:8][CH3:9]>C(OCC)(=O)C>[CH2:6]([C:10]1[N:11]([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:12]2[C:17]([CH3:18])=[C:16]([CH3:19])[N:15]=[C:14]([NH2:5])[C:13]=2[N:27]=1)[CH2:7][CH2:8][CH3:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A sealed tube containing ammonium acetate (7.5 g) and 2-butyl-6,7-dimethyl-4-phenoxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]pyridine (0.75 g) from Part C was heated in an oil bath to 150° C. for 48hours. The reaction reached 70% completion and was allowed to cool to room temperature. The reaction mixture was then dissolved in ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The product was passed through a silica gel column using 10/90 methanol/ethyl acetate as the eluant. To remove impurities, the product was recrystallized twice from acetonitrile with charcoal. The resulting white crystals were crushed and dried to yield 2-butyl-6,7-dimethyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]pyridin-4-amine, m.p. 130.0-132.0° C.
Workup
- temperatureto cool to room temperature
- washwashed with a saturated aqueous solution of sodium bicarbonate
- dry with materialThe organic layer was dried with magnesium sulfate
- concentrationconcentrated under reduced pressure
- customTo remove impurities
- customthe product was recrystallized twice from acetonitrile with charcoal
- customThe resulting white crystals were crushed
- customdried
Sources & evidence
- ORD record
- ord-c983b45a4ebf4fd383e8480a6dcb1532
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06797718B2
Reaction notes
Loading…