Acetone → HCID 54575147, compound

HRID 2190157Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:25][C:11]3=[N:12][C:13]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[C:14](C(C)=C)[CH:15]=[C:10]3[C:9]=2[C:26]([NH:28][CH3:29])=[O:27])=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:34]CC1.[CH3:38][C:39]([CH3:41])=[O:40]>>[OH:34][CH2:38][C:39]([C:14]1[CH:15]=[C:10]2[C:9]([C:26]([NH:28][CH3:29])=[O:27])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[O:25][C:11]2=[N:12][C:13]=1[N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])([OH:40])[CH3:41]

Participants

Reactant 3

HCID 180Acetone

HCID 82029Methyl morpholine oxide

HCID 54576013HCID 54576013, compound

Product 1

HCID 54575147HCID 54575147, compound

Procedure

To 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide (11 mg, 0.026 mmol) in acetone (1 ml) was added NMO (9.26 mg, 0.079 mmol) and potassium osmate dihydrate (0.971 mg, 2.64 μmol). After LCMS indicated predominant conversion of starting material to product, the reaction mixture was purified by HPLC to afford the title compound. MS (ESI) m/z 452.0 (M+1). 2 rotamers confirmed by 2D NMR: 1H NMR (400 MHz, CD3CN) δ ppm 8.66, 8.64 (s, 1H), 8.04-8.02 (m, 2H), 7.34-7.29 (m, 2H), 6.88 (br s, 1H), 4.16-4.13, 4.06-4.03 (m, 1H), 3.92, 3.88 (br s, 1H), 3.82-3.79 (m, 1H), 3.33, 3.32 (s, 3H), 3.29 (s, 3H), 3.15-3.02 (br s, 1H), 2.93-2.92 (d, 3H)

Workup

customthe reaction mixture was purified by HPLC

Sources & evidence

ORD record: ord-79b7a1e65273454498135b82beb8fe2c
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324239B2

Reaction notes

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