Hydrochloric Acid → (3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride

HRID 2192973Notes

Reaction equation

HRID 2192973 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[C:6](Cl)=[N:7]2.[NH2:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]1.Cl.[O:33]1CCOCC1>C1COCC1>[Cl-:1].[F:17][C:15]1[CH:14]=[CH:13][C:5]2[C:6]([NH:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][NH2+:21][CH2:20]3)=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:2](=[O:33])[C:3]=3[C:4]=2[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 59375375HCID 59375375, compound

Product 1

HCID 67416365(3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 1,6-dichloro-9-fluorobenzo[c]-1,6-naphthyridine (320 mg, 1.2 mmol) in dioxane (8 mL) was added tert-butyl (3R)-3-aminopiperidine-1-carboxylate (960 mg, 4.79 mmol) and heated in a microwave reactor for 1 hr at 125° C. The solution was concentrated to provide the crude solid. The crude material was dissolved in THF (5 mL) and 6 N HCl 5 mL) and heated to 85° C. for 2 hr. Upon cooling the solution solidifies and the reaction mixture was triturated with Et2O and filtered to afford (3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride. LRMS (ESI) calc'd for (C17H18FN4O) [M+H]+, 313.2; found 313.1.

Workup

  1. concentrationThe solution was concentrated
  2. customto provide the crude solid
  3. temperatureUpon cooling the solution
  4. customthe reaction mixture was triturated with Et2O
  5. filtrationfiltered

Sources & evidence

ORD record
ord-2ced445b9f6b473eb8d9b46a16720eb2
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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