HCID 89462621, compound → HCID 89462445, compound

HRID 1771127Notes

Reaction equation

[F:1][C:2]1[C:7]([CH:8]([OH:19])[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[N:12]3)=[C:6]([F:20])[CH:5]=[CH:4][C:3]=1[NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>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][CH:13]=[N:12]3)=[O:19])=[C:6]([F:20])[CH:5]=[CH:4][C:3]=1[NH:21][C:22](=[O:27])[C:23]([CH3:25])([CH3:24])[CH3:26]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-(2,4-difluoro-3-(hydroxy(quinoxalin-6-yl)methyl)phenyl)pivalamide (541 mg, 1.46 mmol, 1.0 eq.) in DCM (10 mL) was added MnO2 (640 mg, 73 mmol, 5.0 eq.). The resulting mixture was stirred at 50° C. overnight. The solid was removed by filtration and the filtrate was concentrated. The resulting residue was purified via flash column chromatography (PE/EA=2/1, v/v) to afford N-(2,4-difluoro-3-(quinoxaline-6-carbonyl)phenyl)pivalamide as a yellow foam (495 mg, 92%).

Workup

customThe solid was removed by filtration
concentrationthe filtrate was concentrated
customThe resulting residue was purified via flash column chromatography (PE/EA=2/1

Sources & evidence

ORD record: ord-a717151de6c24d22a17831abad1032cb
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249110B2

Reaction notes

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