Hydrochloric Acid → HCID 69672897, compound

HRID 1426336Notes

Reaction equation

HRID 1426336 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:7]=[C:6]([O:14][CH:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[CH:5]=1.Cl.O1CCOCC1>C(Cl)Cl>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:11])[F:12])[N:7]=[C:6]([O:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69673461HCID 69673461, compound

Product 1

HCID 69672897HCID 69672897, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-{[4-(methoxymethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy}piperidine-1-carboxylate (40. mg, 0.10 mmol, from Step C) in Methylene chloride (1.0 mL) was added 4.0M Hydrogen chloride in dioxane (0.50 mL, 2.0 mmol). The reaction mixture was stirred for one hour. The solvent was removed in vacuo. The residue was dissolved in DCM, and this solution was washed with saturated sodium bicarbonate, water (2×), brine, dried over sodium sulfate, filtered and concentrated to give product which was used without further purification (30 mg, 100%). 1H NMR (400 MHz, CDCl3) δ 7.18 (s, 1H), 6.84 (s, 1H), 5.19 (tt, J=8.4, 3.6 Hz, 1H), 4.45 (s, 2H), 3.44 (s, 3H), 3.19-3.03 (m, 2H), 2.88-2.70 (m, 2H), 2.13-1.97 (m, 2H), 1.73-1.53 (m, 2H); 19F NMR (376 MHz, CDCl3) δ−68.89 (s); LCMS (M+H)+: 291.1.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in DCM
  3. washthis solution was washed with saturated sodium bicarbonate, water (2×), brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give product which
  8. customwas used without further purification (30 mg, 100%)

Sources & evidence

ORD record
ord-8dc27bc20d03497b930ebac0b1d81745
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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