m-Chloroperbenzoic acid → HCID 59301373, compound

HRID 2236310Notes

Reaction equation

[N:1]1([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[N:17]=[C:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[O:19][C:20]=3[C:21]([F:24])([F:23])[F:22])=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:36]>C(Cl)Cl>[O:36]=[S:4]1[CH2:3][CH2:2][N:1]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[N:17]=[C:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[O:19][C:20]=3[C:21]([F:23])([F:24])[F:22])=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5]1

Participants

Conditions

Temperature: -78 °C

Procedure

2-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (6-thiomorpholin-4-yl-pyridin-3-yl)-amide (30 mg, 0.07 mmol) was dissolved in 3 mL of methylene chloride, and cooled down to −78° C. One equivalent of 3-chloroperoxybenzoic acid (12 mg, 0.07 mmol) was added. The reaction mixture was warmed up to room temperature and stirred for 2 hours. The reaction mixture was concentrated under reduced pressure, and then purified by flash chromatography (Merck silica gel 60, 230-400 mesh, 0-20% methanol in methylene chloride for 25 min) to gave 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [6-(1-oxo-1λ4-thiomorpholin-4-yl)-pyridin-3-yl]-amide as an off-white solid. LCMS calcd for C20H17F3N4O3S (m/e) 450, obsd 451 (M+H).

Workup

temperatureThe reaction mixture was warmed up to room temperature
concentrationThe reaction mixture was concentrated under reduced pressure
custompurified by flash chromatography (Merck silica gel 60, 230-400 mesh, 0-20% methanol in methylene chloride for 25 min)

Sources & evidence

ORD record: ord-223e326471024a72b2cf2671b0fa2a6c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714126B2

Reaction notes

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