Hydrochloric Acid → 1-[2-(4-Amino-1-piperidinyl)ethyl]-7-fluoro-1,5-naphthyridin-2(1H)-one 5-oxide Dihydrochloride

HRID 657083Notes

Reaction equation

HRID 657083 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:28])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][CH2:15]2)=[N+:4]([O-:29])[CH:3]=1.[ClH:30]>C(Cl)Cl.O1CCOCC1>[ClH:30].[ClH:30].[NH2:20][CH:17]1[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][N:9]2[C:10]3[CH:11]=[C:2]([F:1])[CH:3]=[N+:4]([O-:29])[C:5]=3[CH:6]=[CH:7][C:8]2=[O:28])[CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 866353491,1-Dimethylethyl {1-[2-(7-fluoro-5-oxido-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-4-piperidinyl}carbamate

Product 1

HCID 688201601-[2-(4-Amino-1-piperidinyl)ethyl]-7-fluoro-1,5-naphthyridin-2(1H)-one 5-oxide Dihydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

1,1-Dimethylethyl {1-[2-(7-fluoro-5-oxido-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-4-piperidinyl}carbamate (335 mg, 0.824 mmol) was dissolved in DCM (3 mL) and 4M HCl in 1,4-dioxane (0.830 mL (ca. 4 eq.) was added. A further 10 mL DCM was added to disperse the solid, then a further 0.830 mL 4M HCl in 1,4-dioxane was added. The mixture was left at room temperature for 30 minutes, then the solvents were removed under reduced pressure to give title compound as a white solid (315 mg).

Workup

  1. additionto disperse the solid
  2. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-e36512f55dcd4d3baa6b2f6466903785
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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