Potassium Carbonate → 4-tert-Butyloxycarbonylamino-1-(6-methoxy-[1,5]naphthyridin-4-yl)aminocarbonylpiperidine
Reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][CH:3]=1.C1N=CN([C:19]([N:21]2[CH:25]=N[CH:23]=[CH:22]2)=[O:20])C=1.Cl.[C:27]([O:31][C:32]([NH:34][CH:35]1CCNC[CH2:36]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:27]([O:31][C:32]([NH:34][CH:35]1[CH2:23][CH2:22][N:21]([C:19]([NH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=3)[N:5]=[CH:4][CH:3]=2)=[O:20])[CH2:25][CH2:36]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-amino-6-methoxy-[1,5]naphthyridine (Example 400a) (2.1 g, 13.5 mmol) and 4-(dimethylamino)pyridine (1.62 g) in anhydrous chloroform (45 ml) was added N,N-carbonyldiimidazole (3.28 g, 20.1 mmol). The mixture was stirred for 4 h at room temperature, then evaporated and the residue was dissolved in anhydrous DMF (45 ml). 4-tert-Butoxycarbonylaminopiperidine hydrochloride (3.34 g, 13.5 mmol) and potassium carbonate (1.89 g) were added, and the mixture was heated at 70° C. overnight. The mixture was evaporated and the residue was mixed with water (120 ml). The solid was filtered off and dried (3.89 g).
Workup
- customevaporated
- dissolutionthe residue was dissolved in anhydrous DMF (45 ml)
- temperaturethe mixture was heated at 70° C. overnight
- customThe mixture was evaporated
- additionthe residue was mixed with water (120 ml)
- filtrationThe solid was filtered off
- customdried (3.89 g)
Sources & evidence
- ORD record
- ord-0004a56d53d64d0baae3855f59176ad0
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07534793B2
Reaction notes
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