Potassium Carbonate → HCID 86656330, compound

HRID 2200858Notes

Reaction equation

HRID 2200858 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[NH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.C(O)(C)(C)C>[C:28]([O:27][C:25]([N:22]1[CH2:23][CH2:24][CH:19]([NH:18][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=3)[N:5]=[CH:4][C:3]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:20][CH2:21]1)=[O:26])([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 14515789Ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 86656330HCID 86656330, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

Ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate (0.5 g, 1.85 mmol) and tert-butyl 4-aminopiperidine-1-carboxylate (0.45 g, 2.22 mmol) were dissolved in the mixture of DCM (5 mL) and tert-butyl alcohol (5 mL). Potassium carbonate (0.612 g, 4.43 mmol) was added to the solution. The reaction mixture was stirred at ambient temperature for 24 h and filtrated under reduced pressure. The solid was washed by DCM. The filtrate was concentrated under reduced pressure. The residue was recrystallized in diethyl ether to give a faint yellow solid (0.73 g, 90.9% yield).

Workup

  1. filtrationfiltrated under reduced pressure
  2. washThe solid was washed by DCM
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was recrystallized in diethyl ether

Sources & evidence

ORD record
ord-ff5c8b68c8984ae0aadc5a71b597316c
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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