Trifluoroacetic acid → HCID 86730280, compound

HRID 1850225Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[CH:5]=[CH:4][N:3]=1.[F:17][C:18]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=1[C@@H:25]([NH2:27])[CH3:26].CCN(C(C)C)C(C)C.C(O)(C(F)(F)F)=O>CS(C)=O>[F:17][C:18]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=1[C@@H:25]([NH:27][C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[CH:5]=[CH:4][N:3]=1)[CH3:26]

Participants

Conditions

Temperature: 110 °C

Procedure

To a microwave vial with stir bar was added (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (24.96 mg, 0.103 mmol) in DMSO (1653 μL). To this reaction mixture was added (S)-1-(2,3-difluorophenyl)ethanamine (40 mg, 0.207 mmol) and DIEA (144 μL, 0.826 mmol). The vial capped and heated at 110° C. over the weekend. The solution was filtered, then purified by reverse phase HPLC. Product fractions combined, frozen and lyopholyzed to afford ((S)-3-(2-((S)-1-(2,3-difluorophenyl)ethylamino) pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (10.2 mg, 0.021 mmol, 10.26% yield) as a TFA salt. 1H NMR (400 MHz, CD3OD) δ ppm 0.59 (br. s., 3H) 0.75 (br. s., 3H) 1.59 (d, J=6.99 Hz, 3H) 1.69 (br. s., 1H) 4.37 (d, J=5.67 Hz, 2H) 4.66 (br. s., 1H) 5.40 (d, J=7.38 Hz, 1H) 7.06-7.23 (m, 3H) 7.70 (d, J=6.90 Hz, 1H) 8.14 (d, J=6.46 Hz, 1H); LCMS m/z 363.3 (M+H)+, Rt 0.77 min.; HRMS(A) m/z 363.1642 (M+H)+, Rt 1.89 min.

Workup

customThe vial capped
filtrationThe solution was filtered
custompurified by reverse phase HPLC
temperaturefrozen

Sources & evidence

ORD record: ord-49fab11c73b54152bce6519214efa47d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957068B2

Reaction notes

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