Water → Trifluoroacetic acid

HRID 1850235Notes

Reaction equation

HRID 1850235 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][O:10][C:9]2=[O:19])[CH:5]=[CH:4][N:3]=1.[F:20][C:21]([F:26])([F:25])[CH:22]([NH2:24])[CH3:23].CCN(C(C)C)C(C)C.[OH2:36]>CS(C)=O>[C:13]1([C@H:12]2[CH2:11][O:10][C:9](=[O:19])[N:8]2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:24][CH:22]([CH3:23])[C:21]([F:26])([F:25])[F:20])[N:7]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F:20][C:21]([F:26])([F:25])[C:22]([OH:10])=[O:36]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 37831651,1,1-Trifluoro-2-propanamineHCID 89479380(4S)-3-(2-Chloro-4-pyrimidinyl)-4-phenyl-2-oxazolidinone

Product 2

HCID 6422Trifluoroacetic acidHCID 90342888HCID 90342888, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
115 °C

Procedure

A mixture of (S)-3-(2-chloropyrimidin-4-yl)-4-phenyloxazolidin-2-one (40 mg, 0.145 mmol), 1,1,1-trifluoropropan-2-amine (82 mg, 0.725 mmol), Hunig's Base (0.038 mL, 0.218 mmol) in DMSO (0.4 mL) was heated under argon at 115° C. for ˜3 days. Then mixture was allowed to cool to room temperature. The mixture was diluted with DMSO and water (˜10 vol. % of DMSO), filtered through a syringe filter and purified by reverse phase HPLC. Selected fractions were collected and lyophilized providing (45)-4-phenyl-3-(2-(1,1,1-trifluoropropan-2-ylamino)pyrimidin-4-yl)oxazolidin-2-one (ratio of two isomers: 7/3) as white solid as its trifluoroacetic acid salt. LCMS m/z 353.2 (M+H)+, Rt 0.78 min. HRMS(A) m/z 353.1231 (M+H)+, Rt 1.92/1.96 min.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through a syringe
  3. filtrationfilter
  4. custompurified by reverse phase HPLC
  5. customSelected fractions were collected

Sources & evidence

ORD record
ord-9fdd6f2f63414e4698a9e8601434180d
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

Loading…