HCID 66971140, compound → HCID 66900404, compound

HRID 905557Notes

Reaction equation

HRID 905557 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:18]2[C:19]([F:30])=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]=[C:25]([O:28][CH3:29])[CH:24]=[CH:23]3)[CH2:16][OH:17])[CH2:10][CH2:9]1)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:18]2[C:19]([F:30])=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]=[C:25]([O:28][CH3:29])[CH:24]=[CH:23]3)[CH2:16][OH:17])[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 66971140HCID 66971140, compound

Product 1

HCID 66900404HCID 66900404, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of rac-{1-[2-(7-fluoro-2-methoxy-quinolin-8-yl) -3-hydroxy-propyl]-piperidin-4-yl}-carbamic acid tert-butyl ester (WO 2007/081597, 1.42 g, 3.28 mmol) in a mixture of TFA (15 mL) and DCM (9 mL) was stirred at rt for 20 min. The solvent was removed in vacuo and the residue was diluted in sat. NaHCO3 (20 mL). The pH was adjusted to 12 adding 6M NaOH. The aq. layer was extracted 3 times with DCM-MeOH (9-1, 3×25 mL). The combined org. layers were washed once with brine (20 mL), dried over Na2SO4, filtered and concentrated to dryness to afford the title amine as a yellowish gum (1.1 g, 100% yield).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted in sat. NaHCO3 (20 mL)
  3. extractionThe aq. layer was extracted 3 times with DCM-MeOH (9-1, 3×25 mL)
  4. washlayers were washed once with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-87f58de2a5434bd5a79c110760759e7f
Source dataset
uspto-grants-2011_09
Patent number
US08012961B2

Reaction notes

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