N-(2,4,5-trifluoro-3-(hydroxy(3-morpholinoquinoxalin-6-yl)methyl)phenyl)pivalamide → N-(2,4,5-trifluoro-3-(3-morpholinoquinoxaline-6-carbonyl)phenyl)pivalamide

HRID 929348Notes

Reaction equation

[F:1][C:2]1[C:7]([CH:8]([OH:25])[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][C:13]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[N:12]3)=[C:6]([F:26])[C:5]([F:27])=[CH:4][C:3]=1[NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]>C(Cl)Cl.O=[Mn]=O>[F:1][C:2]1[C:7]([C:8]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][C:13]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[N:12]3)=[O:25])=[C:6]([F:26])[C:5]([F:27])=[CH:4][C:3]=1[NH:28][C:29](=[O:34])[C:30]([CH3:32])([CH3:31])[CH3:33]

Participants

Conditions

Temperature: 50 °C

Procedure

The solution of N-(2,4,5-trifluoro-3-(hydroxy(3-morpholinoquinoxalin-6-yl)methyl)phenyl)pivalamide (620 mg, 1.3 mmol, 1.0 eq.) in DCM (10 mL) was added MnO2 (358 mg, 6.5 mmol, 5.0 eq.). The resulting mixture was stirred at 50° C. overnight, then cooled and filtered. The filtrate was concentrated and the residue was purified by flash column chromatography (PE/EA=1/2, v/v) to afford N-(2,4,5-trifluoro-3-(3-morpholinoquinoxaline-6-carbonyl)phenyl)pivalamide (560 mg, 90%).

Workup

temperaturecooled
filtrationfiltered
concentrationThe filtrate was concentrated
customthe residue was purified by flash column chromatography (PE/EA=1/2

Sources & evidence

ORD record: ord-b15cdde9621a4076880360c1472a1d79
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09295671B2

Reaction notes

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