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

HRID 656978Notes

Reaction equation

HRID 656978 reaction equation
[OH:1][C@H:2]1[C@@H:7]([NH:8]C(=O)OC(C)(C)C)[CH2:6][CH2:5][N:4]([CH2:16][CH2:17][N:18]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=3)[CH:21]=[CH:20][C:19]2=[O:30])[CH2:3]1.[ClH:31]>C(Cl)Cl.O1CCOCC1>[ClH:31].[ClH:31].[NH2:8][C@H:7]1[CH2:6][CH2:5][N:4]([CH2:16][CH2:17][N:18]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=3)[CH:21]=[CH:20][C:19]2=[O:30])[CH2:3][C@H:2]1[OH:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 585794481,1-dimethylethyl ((3R,4S)-3-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-4-piperidinyl)carbamate

Product 1

HCID 674980421-{2-[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]ethyl}-7-(methyloxy)-1,5-naphthyridin-2(1H)-one Dihydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-dimethylethyl ((3R,4S)-3-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1 (2H)-yl]ethyl}-4-piperidinyl)carbamate (258 mg, 0.6165 mmol) was dissolved in DCM (10 mL) and the solution was treated with 4M hydrogen chloride in 1,4-dioxane (2 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 the title compound as a pale pink solid (223 mg).

Workup

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

Sources & evidence

ORD record
ord-5e0ea18b1ca34e2795f2d64e48c3c8ce
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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