Potassium Carbonate → HCID 53251550, compound

HRID 1028091Notes

Reaction equation

Br[C:2]1[S:3][C:4]([C:7]2[CH:8]=[C:9]([NH:13][C:14]3[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:5][N:6]=1.C([O-])([O-])=O.[K+].[K+].[O:30]1[CH2:34][CH2:33][NH:32][C:31]1=[O:35].CN(C)CCN>C(OCC)(=O)C.[Cu](I)I.O1CCOCC1>[F:21][C:20]([F:23])([F:22])[C:18]1[CH:17]=[CH:16][N:15]=[C:14]([NH:13][C:9]2[CH:8]=[C:7]([C:4]3[S:3][C:2]([N:32]4[CH2:33][CH2:34][O:30][C:31]4=[O:35])=[N:6][CH:5]=3)[CH:12]=[CH:11][CH:10]=2)[N:19]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To N-[3-(2-bromo-1,3-thiazol-5-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (180 mg, 0.449 mmol) were added copper iodide (17.09 mg, 0.090 mmol), K2CO3 (124 mg, 0.897 mmol), 1,3-oxazolidin-2-one (78 mg, 0.897 mmol) and dioxane. N,N-dimethylethane-1,2-diamine (7.91 mg, 0.090 mmol) was added and the reaction was allowed to stir at 110° C. for 4 hours. The reaction mixture was diluted with ethyl acetate washed with brine, dried over Na2SO4 and concentrated in vacuo. The product was purified by column chromatography on silica gel (50-70% ethyl acetate/hexane) to afford 3-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,3-oxazolidin-2-one (98 mg, 54%) as an off-white solid. APCI [M+H]+ m/z 408.0. 1H NMR (500 MHz, CDCl3): δ 8.71 (d, J=4.9 Hz, 1H); 8.08 (s, 1H); 7.69 (s, 1H); 7.51 (d, J=8.1 Hz, 1H); 7.43-7.38 (m, 2H); 7.30 (s, 1H); 7.11 (d, J=4.9 Hz, 1H); 4.68 (t, J=8.1 Hz, 2H); 4.39 (t, J=8.1 Hz, 2H). rhSYK activity=+++.

Workup

washwashed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe product was purified by column chromatography on silica gel (50-70% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-964a959d2e47424c89b173173616f5da
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735417B2

Reaction notes

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