Hydrochloric Acid → 1-{2-[(3S,4R)-4-amino-3-hydroxy-1-piperidinyl]ethyl}-7-fluoro-1,5-naphthyridin-2(1H)-one dihydrochloride

HRID 657010Notes

Reaction equation

HRID 657010 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:29])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][C@@H:17]([NH:20]C(=O)OC(C)(C)C)[C@@H:16]([OH:28])[CH2:15]2)=[N:4][CH:3]=1.[ClH:30]>C(Cl)Cl.O1CCOCC1>[ClH:30].[ClH:30].[NH2:20][C@@H:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][N:9]2[C:10]3[C:5](=[N:4][CH:3]=[C:2]([F:1])[CH:11]=3)[CH:6]=[CH:7][C:8]2=[O:29])[CH2:15][C@@H:16]1[OH:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866353331,1-dimethylethyl {(3S,4R)-1-[2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-3-hydroxy-4-piperidinyl}carbamate

Product 1

HCID 689924211-{2-[(3S,4R)-4-amino-3-hydroxy-1-piperidinyl]ethyl}-7-fluoro-1,5-naphthyridin-2(1H)-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl {(3S,4R)-1-[2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-3-hydroxy-4-piperidinyl}carbamate (310 mg, 0.7627 mmol) was dissolved in DCM (1 ml) and the solution was treated with 4M hydrogen chloride in 1,4-dioxane (1 ml). Effervescence and formation of a precipitate was observed. After 2 h, the solvents were removed under reduced pressure and the residue was dried under reduced pressure overnight, to give 1-{2-[(3S,4R)-4-amino-3-hydroxy-1-piperidinyl]ethyl}-7-fluoro-1,5-naphthyridin-2(1H)-one dihydrochloride as an off-white solid (253 mg).

Workup

  1. customthe solvents were removed under reduced pressure
  2. customthe residue was dried under reduced pressure overnight

Sources & evidence

ORD record
ord-c970d983f5be4882850246478c7f4124
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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