Water → 1-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
Reaction equation
N[C:2]1[C:3]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][N:18](C(OC)=O)[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1.ClC(Cl)(O[C:29](=[O:35])[O:30][C:31](Cl)(Cl)Cl)Cl.C([N:39]([CH2:42]C)CC)C.[OH2:44]>O1CCCC1>[CH3:31][O:30][C:29]([N:18]1[CH2:17][CH2:16][CH:15]([N:12]2[CH2:11][CH2:10][CH:9]([N:8]3[C:6]4[C:5](=[N:39][CH:42]=[CH:2][CH:7]=4)[NH:4][C:3]3=[O:44])[CH2:14][CH2:13]2)[CH2:20][CH2:19]1)=[O:35]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Twenty (20) mg of 3-amino-2-[1-(1-methoxycarbonylpiperidin-4-yl)piperidin-4-yl]aminopyridin and 18 mg of triphosgene were dissolved in 2 ml of tetrahydrofuran, and to which 45 μl of triethylamine was added under cooling with ice. The system was further stirred at the same temperature for 2 hours and for an hour, at room temperature. Thereafter water was added to the reaction liquid and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, concentrated and the resulting crude product was purified by silica gel chromatography (chloroform/methanol=10/1) to give 12 mg of the title compound.
Workup
- temperatureunder cooling with ice
- extractionextracted with chloroform
- dry with materialThe extract was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customthe resulting crude product was purified by silica gel chromatography (chloroform/methanol=10/1)
Sources & evidence
- ORD record
- ord-51729313193b4899bcf2d02b4d802fee
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06699880B1
Reaction notes
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