tert-butyl (1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate → 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:29])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[N:5][CH:4]=1>C(Cl)(Cl)Cl.FC(F)(F)C(O)=O>[NH2:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[N:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH:7]=[CH:8][C:9]2=[O:29])[CH2:20][CH2:19]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4.36 g of tert-butyl (1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate in 50 mL of chloroform, 10 mL of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 1 hour. After the solvent was distilled off under reduced pressure, the reaction mixture was alkalified with a saturated aqueous sodium hydrogen carbonate solution, the solvent was then distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography using silica gel; Chromatorex-NH made by Fuji Silysia Chemical Ltd., and an eluent of chloroform:methanol=10:1 to obtain 2.16 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one as a yellow oily substance.
Workup
- distillationAfter the solvent was distilled off under reduced pressure
- distillationthe solvent was then distilled off under reduced pressure
- customthe resultant residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-c02b1d33b2cb4f7aaa628d30df94eccf
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367831B2
Reaction notes
Loading…