Acetone → HCID 54575147、化合物

HRID 2190157ノート

反応式

[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]

参加物

反応物 3

HCID 180Acetone

HCID 82029Methyl morpholine oxide

HCID 54576013HCID 54576013、化合物

生成物 1

HCID 54575147HCID 54575147、化合物

実験手順

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)

後処理

customthe reaction mixture was purified by HPLC

出典と根拠

ORDレコード: ord-79b7a1e65273454498135b82beb8fe2c
出典データセット: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08324239B2

反応ノート

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