Potassium Carbonate → rac-4-(5-cyano-7-isopropylbenzo[d]oxazol-2-yl)-N-((2-oxo-3-(5-(2-(trifluoromethoxy)phenyl)pyridin-2-yl)oxazolidin-5-yl)methyl)benzamide

HRID 2066804Notes

Reaction equation

HRID 2066804 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH:11]([CH2:13][NH:14][C:15](=[O:36])[C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:23][C:24]5[C:30]([CH:31]([CH3:33])[CH3:32])=[CH:29][C:28]([C:34]#[N:35])=[CH:27][C:25]=5[N:26]=4)=[CH:18][CH:17]=3)[O:10][C:9]2=[O:37])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:44][C:45]([F:57])([F:56])[O:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1B(O)O>O1CCCC1.O.C(P([C-]1C=CC=C1)C(C)(C)C)(C)(C)C.[CH-]1C=CC=C1.[Fe+2].[Pd]>[C:34]([C:28]1[CH:29]=[C:30]([CH:31]([CH3:33])[CH3:32])[C:24]2[O:23][C:22]([C:19]3[CH:20]=[CH:21][C:16]([C:15]([NH:14][CH2:13][CH:11]4[O:10][C:9](=[O:37])[N:8]([C:5]5[CH:4]=[CH:3][C:2]([C:48]6[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=6[O:46][C:45]([F:44])([F:57])[F:56])=[CH:7][N:6]=5)[CH2:12]4)=[O:36])=[CH:17][CH:18]=3)=[N:26][C:25]=2[CH:27]=1)#[N:35]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27772042-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 25151662rac-N-((3-(5-chloropyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)-4-(5-cyano-7-isopropylbenzo[d]oxazol-2-yl)benzamide

Product 1

HCID 25108843rac-4-(5-cyano-7-isopropylbenzo[d]oxazol-2-yl)-N-((2-oxo-3-(5-(2-(trifluoromethoxy)phenyl)pyridin-2-yl)oxazolidin-5-yl)methyl)benzamideYield 83%

Reagents, catalysts & solvents 3

HCID 178454864HCID 178454864, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of N-{[3-(5-chloropyridin-2-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide (52 mg) and potassium carbonate (55 mg) in 1 ml of tetrahydrofuran and 1 ml of water was added 2-trifluoromethoxyphenylboronic acid (82 mg) and palladium di-tert-butylphosphinoferrocene (13 mg). The mixture was heated via microwave for 15 min at 150° C. The sample was cooled to room temperature, and purified was purified via column chromatography on a Biotage Horizon 40M column eluting with 0% ethyl acetate in hexanes (1 column volumes), followed by a gradient to 100% ethyl acetate in hexanes (over 10 column volumes), and held at 100% ethyl acetate for 3 column volumes to provide the title compound as an off-white solid (53 mg, 83%). Mass spectrum (ESI) 642.2 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.43 (s, 1H), 8.35 (d, J=7.8 Hz, 2H), 8.28 (d, J=8.7 Hz, 1H), 7.98 (d, J=8.3 Hz, 2H), 7.94 (s, 1H), 7.84 (d, J=8.7 Hz, 1H), 7.52 (s, 1H), 7.40 (m, 4H), 6.76 (bs, 1H), 4.98 (m, 1H), 4.48 (dd, J=9.1 Hz, 10.7 Hz, 1H), 4.13 (m, 2H), 3.72 (m, 1H), 3.49 (sept, J=6.9 Hz, 1H), 1.46 (d, J=7.1 Hz, 6H).

Workup

  1. temperatureThe sample was cooled to room temperature
  2. custompurified
  3. customwas purified via column chromatography on a Biotage Horizon 40M column
  4. washeluting with 0% ethyl acetate in hexanes (1 column volumes)

Sources & evidence

ORD record
ord-593d9da592db42b5bd197e38d76a001f
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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