Hydrogen Bromide → HCID 68498399, compound

HRID 1963450Notes

Reaction equation

HRID 1963450 reaction equation
[O:1]=[C:2]1[CH:6]=[C:5]([C@@H:7]2[CH2:12][CH2:11][N:10](C(OC)=O)[C@@H:9]([C:17]3[CH:22]=[C:21]([F:23])[C:20]([F:24])=[C:19]([F:25])[CH:18]=3)[CH2:8]2)[O:4][NH:3]1.Br>>[F:25][C:19]1[CH:18]=[C:17]([C@H:9]2[CH2:8][C@H:7]([C:5]3[O:4][NH:3][C:2](=[O:1])[CH:6]=3)[CH2:12][CH2:11][NH:10]2)[CH:22]=[C:21]([F:23])[C:20]=1[F:24]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 131730418HCID 131730418, compound

Product 1

HCID 68498399HCID 68498399, compoundYield 25%

Procedure

Trans-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3,4,5-trifluorophenyl)piperidine-1-carboxylate (53.4 mg, 0.15 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 1.18 mL, 6.75 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-(3,4,5-trifluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (11 mg, 25%). 1H NMR (600 MHz, dmso) δ 1.72-1.88 (m, 3H), 1.97-2.04 (m, 1H), 2.61-2.69 (m, 1H), 2.76-2.83 (m, 1H), 3.06-3.11 (m, 1H), 3.69-3.75 (m, 1H), 5.98 (s, 1H), 7.28-7.36 (m, 2H). HRMS Calculated for [C14H13F3N2O2+H]+: 299.1007. Found: 299.1031

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-261c81f54d74493cbbf2cafefe1e6827
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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