Hydrochloric Acid → HCID 22499148, compound
Reaction equation
[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:19][CH2:20][CH3:21])[N:10]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15]C(=O)C)[C:6]=2[C:5]([CH3:22])=[C:4]([CH3:23])[N:3]=1.Cl>>[NH2:15][CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[C:6]2[C:5]([CH3:22])=[C:4]([CH3:23])[N:3]=[C:2]([NH2:1])[C:7]=2[N:8]=[C:9]1[CH2:19][CH2:20][CH3:21]Participants
Conditions
- Temperature
- 100 °C
Procedure
N-[4-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]acetamide was combined with 6 N hydrochloric acid (75 mL) in a pressure vessel. The vessel was sealed and then heated at 100° C. overnight. An additional 1 mL of 6 N hydrochloric acid was added and heating was continued for 6 more hours. The reaction mixture was allowed to cool to ambient temperature overnight and then it was extracted with ethyl acetate (×2). The aqueous layer was cooled in an ice bath, made basic (pH 13) with 50% sodium hydroxide, saturated with sodium chloride, and then extracted with chloroform (×3). The combined organics were washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure to provide 0.98 g of 1-(4-aminobutyl)-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine as a tan solid.
Workup
- customThe vessel was sealed
- temperatureheating
- temperatureto cool to ambient temperature overnight
- extractionit was extracted with ethyl acetate (×2)
- temperatureThe aqueous layer was cooled in an ice bath
- extractionsaturated with sodium chloride, and then extracted with chloroform (×3)
- washThe combined organics were washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6f30f3b71d94482583d2acb4c6c93cb9
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06878719B2
Reaction notes
Loading…