Hydrochloric Acid → (2-{4-[3-Fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-1-piperazinyl}ethyl)amine

HRID 2356332Notes

Reaction equation

HRID 2356332 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[CH2:14][CH2:13]1)=[N:9][C:8]([O:28][CH3:29])=[CH:7][CH:6]=2.Cl.O1CCOCC1>CO>[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][NH2:20])[CH2:14][CH2:13]1)=[N:9][C:8]([O:28][CH3:29])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 575995761,1-Dimethylethyl (2-{4-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-1-piperazinyl}ethyl)carbamate

Product 1

HCID 57599574(2-{4-[3-Fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-1-piperazinyl}ethyl)amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl (2-{4-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-1-piperazinyl}ethyl)carbamate (725 mg, 1.79 mmol) in MeOH (9 mL) at 25° C. was added dropwise a 4M solution of HCl in dioxane (3.1 mL, 12.53 mmol). After 12 h, the solution was concentrated the residue neutralized using excess MP carbonate resin in DCM affording the free amine which was used without further purification: LCMS (ES) m/e 306 (M+H)+.

Workup

  1. concentrationthe solution was concentrated the residue neutralized using excess MP carbonate resin in DCM affording the free amine which
  2. customwas used without further purification

Sources & evidence

ORD record
ord-0c78bedf9a394df0bacb0fece5ab5b75
Source dataset
uspto-grants-2010_07
Patent number
US07759340B2

Reaction notes

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