Hydrogen Bromide → HCID 66732155, compound

HRID 1963403Notes

Reaction equation

HRID 1963403 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:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=3)[CH2:8]2)[O:4][NH:3]1.Br>>[F:26][C:23]([F:24])([F:25])[C:20]1[N:19]=[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][CH:21]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 131730400HCID 131730400, compound

Product 1

HCID 66732155HCID 66732155, compoundYield 23%

Procedure

Trans-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)-piperidine-1-carboxylate (60 mg, 0.16 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 1.27 mL, 7.27 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-(6-(trifluoromethyl)pyridin-3-yl)piperidin-4-yl)isoxazol-3(2H)-one (11.4 mg, 23%), 1H NMR (400 MHz, dmso) δ 1.77-1.99 (m, 3H), 2.06-2.16 (m, 1H), 2.69-2.80 (m, 1H), 2.83-2.94 (m, 1H), 3.07-3.59 (m, 1H), 3.94 (d, 1H), 6.03 (s, 1H), 7.86 (d, 1H), 8.08 (d, 1H), 8.78 (s, 1H). HRMS Calculated for [C14H14F3N3O2+H]+: 314.1116. Found: 314.1122

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-c16bf517215c48e7a58b31dcddb093b8
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…