Methyl morpholine oxide → HCID 59333301, compound

HRID 1893482Notes

Reaction equation

[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:13]=C)[N:9]1[CH:15]=[CH:16][N:17]=[C:8]1[C:7]([NH:18][CH2:19][CH2:20][CH2:21][OH:22])=[N:6]2.C[N+]1([O-])CC[O:29]CC1.I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[OH:22][CH2:21][CH2:20][CH2:19][NH:18][C:7]1[C:8]2[N:9]([CH:15]=[CH:16][N:17]=2)[C:10]2[C:5]([N:6]=1)=[CH:4][C:3]([C:2]([F:1])([F:23])[F:24])=[C:12]([CH:13]=[O:29])[CH:11]=2

Participants

Conditions

Temperature: 30 °C

Procedure

A solution of 3-{[7-(trifluoromethyl)-8-vinylimidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol (110 mg; 0.32 mmol; 1 eq), osmium tetroxide (2.5% in tert-butanol, 166 mg; 0.016 mmol; 0.05 eq), N-methylmorpholine oxide (76 mg; 0.654 mmol; 2 eq) in acetone (3 ml) and water (0.33 ml) is stirred at 30° C. during 3 days. A suspension of sodium periodate (280 mg; 1.31 mmol; 4 eq) in water (1.6 ml) is then added and the resulting reaction mixture is stirred at 30° C. during 16 h. Partition (aqueous sodium sulfite/ethyl acetate), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying (magnesium sulphate) and purification by prep CCM on silicagel (dichloromethane/methanol 95:5) affords the title product as an off-white powder (64 mg; 0.19 mmol; 59%).

Workup

additionis then added
customthe resulting reaction mixture
customPartition
extraction(aqueous sodium sulfite/ethyl acetate), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases
customdrying
custom(magnesium sulphate) and purification by prep CCM on silicagel (dichloromethane/methanol 95:5)

Sources & evidence

ORD record: ord-d1692fab047747239e859581b8780fc9
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513250B2

Reaction notes

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