Acetaldehyde → 4-[5,7-dimethyl-4-(3,4,5-trimethoxyphenoxy)imidazo[5,1-f][1,2,4]triazin-2-yl]-N,N-diethylaniline
Reaction equation
[C:1]([BH3-])#[N:2].[Na+].[CH:5](=O)[CH3:6].[CH3:8][C:9]1[N:10]=[C:11]([CH3:38])[N:12]2[C:17]=1[C:16]([O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1)=[N:15][C:14]([C:31]1[CH:37]=[CH:36][C:34](N)=[CH:33][CH:32]=1)=[N:13]2.Cl.[CH3:40]O>>[CH3:8][C:9]1[N:10]=[C:11]([CH3:38])[N:12]2[C:17]=1[C:16]([O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1)=[N:15][C:14]([C:31]1[CH:37]=[CH:36][C:34]([N:2]([CH2:1][CH3:40])[CH2:5][CH3:6])=[CH:33][CH:32]=1)=[N:13]2Participants
6
Conditions
- Temperature
- 20 °C
Procedure
10 mg (0.08 mmol) of sodium cyanoborohydride and 10 mg (0.17 mmol) of acetaldehyde are added to a solution of 40 mg (0.08 mmol) of 4-[5,7-dimethyl-4-(3,4,5-trimethoxyphenoxy)imidazo[5,1-f][1,2,4]triazin-2-yl]aniline from example 1 in methanol and the mixture is stirred at 20° C. After expiration of the reaction time, the mixture is treated with 2N hydrochloric acid. The methanol is removed under reduced pressure and the aqueous residue is washed with dichloromethane, rendered alkaline using sodium hydroxide, and extracted twice with dichloromethane. The organic phase is dried over sodium sulfate and purified by chromatography (eluent:dichloromethane/methanol 80:1-60:1-40:1 plus a drop of NH4OH)
Workup
- customThe methanol is removed under reduced pressure
- washthe aqueous residue is washed with dichloromethane
- extractionextracted twice with dichloromethane
- dry with materialThe organic phase is dried over sodium sulfate
- custompurified by chromatography (eluent
Sources & evidence
- ORD record
- ord-4a8bde4e1b044c9fbc9d6f89afadb3f7
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07202243B2
Reaction notes
Loading…