Hydrogen Bromide → HCID 66732460, compound

HRID 1963467Notes

Reaction equation

HRID 1963467 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C@H:12]2[CH2:17][C@H:16]([C:18]3[O:22][NH:21][C:20](=[O:23])[CH:19]=3)[CH2:15][CH2:14][N:13]2C(OC)=O)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].Br>>[CH3:1][C:2]1[CH:3]=[C:4]([C@H:12]2[CH2:17][C@H:16]([C:18]3[O:22][NH:21][C:20](=[O:23])[CH:19]=3)[CH2:15][CH2:14][NH:13]2)[CH:5]=[CH:6][C:7]=1[C:8]([F:9])([F:10])[F:11]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 131730426HCID 131730426, compound

Product 1

HCID 66732460HCID 66732460, compoundYield 64%

Procedure

Trans-methyl 2-(3-methyl-4-(trifluoromethyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.139 g, 0.36 mmol) was dissolved in HBr (33% in acetic acid, 5.60 g, 22.84 mmol) and the mixture was stirred at room temperature overnight. The solvent was evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-(trans-2-(3-methyl-4-(trifluoromethyl)phenyl)piperidin-4-yl)isoxazol-3(2H)-one (0.075 g, 64%). 1H NMR (600 MHz, dmso) δ 1.76-1.85 (m, 2H), 1.85-1.93 (m, 1H), 1.99-2.07 (m, 1H), 2.40 (d, 2H), 2.67-2.75 (m, 1H), 2.80-2.89 (m, 1H), 3.10-3.17 (m, 1H), 3.68-3.78 (m, 1H), 5.96 (s, 1H), 7.36 (d, 1H), 7.43 (s, 1H), 7.57 (d, 1H). HRMS Calcd for [C16H17F3N2O2+H]+: 327.1320. Found: 327.1298.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm)

Sources & evidence

ORD record
ord-d555c42b7990411e98d87b1ba4e866ec
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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