Trifluoroacetic acid → HCID 71542386, compound

HRID 1850222Notes

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[CH:23]=[C:22]([C:24]2([CH3:27])[CH2:26][CH2:25]2)[CH:21]=[CH:20][C:19]=1[C@@H:28]([NH2:30])[CH3:29].CCN(C(C)C)C(C)C.C(O)(C(F)(F)F)=O>CS(C)=O>[F:17][C:18]1[CH:23]=[C:22]([C:24]2([CH3:27])[CH2:25][CH2:26]2)[CH:21]=[CH:20][C:19]=1[C@@H:28]([NH:30][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)[CH3:29]

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 (30 mg, 0.12 mmol) and DMSO (1 mL). To this reaction mixture was added (S)-1-(2-fluoro-4-(1-methylcyclopropyl)phenyl)ethanamine (51 mg, 0.22 mmol) and DIEA (0.09 ml, 0.50 mmol). The vial was capped and the reaction mixture was heated in a preheated oil bath at 110° C. for 18 hr. Solution was purified by reverse phase HPLC. Product fractions combined, frozen and lyophilized to afford (S)-3-(2-((S)-1-(2-fluoro-4-(1-methylcyclopropyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (3.3 mg, 6.3 μmol, 5% yield) as a TFA salt. 1H NMR (400 MHz, CD3OD) δ 0.58 (br. s., 3H) 0.77 (td, J=5.23, 1.76 Hz, 5H) 0.80-0.86 (m, 2H) 1.38 (s, 3H) 1.57 (d, J=6.94 Hz, 3H) 4.34-4.41 (m, 2H) 4.67 (br. s., 1H) 5.33 (d, J=7.97 Hz, 1H) 6.95-7.05 (m, 2H) 7.22 (t, J=7.97 Hz, 1H) 7.67 (d, J=6.85 Hz, 1H) 8.14 (d, J=6.65 Hz, 1H). LCMS m/z 399.4 (M+H)+, Rt 0.93 min. HRMS(A) m/z 399.2202 (M+H)+, Rt 2.23 min.

Workup

customThe vial was capped
customSolution was purified by reverse phase HPLC
temperaturefrozen

Sources & evidence

ORD record: ord-49f3818bc1a0459fb13e39f54bc2924d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957068B2

Reaction notes

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