Hydrochloric Acid → (2R,3S)-3-amino-8-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]decan-2-ol

HRID 734233Notes

Reaction equation

HRID 734233 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[N:12]1[CH2:30][CH2:29][C:15]3([CH2:19][C@H:18]([NH:20]C(=O)OC(C)(C)C)[C@H:17]([OH:28])[CH2:16]3)[CH2:14][CH2:13]1)=[N:9][C:8]([O:31][CH3:32])=[CH:7][CH:6]=2.Cl.O1CCOCC1>CO>[NH2:20][C@H:18]1[CH2:19][C:15]2([CH2:29][CH2:30][N:12]([C:11]3[C:10]4[C:5](=[CH:6][CH:7]=[C:8]([O:31][CH3:32])[N:9]=4)[N:4]=[CH:3][C:2]=3[F:1])[CH2:13][CH2:14]2)[CH2:16][C@H:17]1[OH:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 578429281,1-dimethylethyl {(2S,3R)-8-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-3-hydroxy-8-azaspiro[4.5]dec-2-yl}carbamate

Product 1

HCID 57842929(2R,3S)-3-amino-8-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]decan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl {(2S,3R)-8-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-3-hydroxy-8-azaspiro[4.5]dec-2-yl}carbamate (0.92 mg, 0.206 mmol) in MeOH (2 mL) at 25° C. was added dropwise a 4M solution of HCl in dioxane (360 μL, 1.40 mmol). After 12 h, the solution was concentrated the residue neutralized using excess MP carbonate resin in DCM affording the free amine (26 mg, 36%) which was used without further purification: LCMS (ES) m/e 347 (M+H)+.

Workup

  1. concentrationthe solution was concentrated the residue neutralized using excess MP carbonate resin in DCM affording the free amine (26 mg, 36%) which
  2. customwas used without further purification

Sources & evidence

ORD record
ord-f001d1e32c0c47738351d5470a7b8a24
Source dataset
uspto-grants-2009_09
Patent number
US07592334B2

Reaction notes

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