Acetone → HCID 54575147, 화합물

HRID 2190157노트

반응식

[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]

참가 물질

반응물 3

HCID 180Acetone

HCID 82029Methyl morpholine oxide

HCID 54576013HCID 54576013, 화합물

생성물 1

HCID 54575147HCID 54575147, 화합물

실험 절차

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)

후처리

customthe reaction mixture was purified by HPLC

출처 및 근거

ORD 기록: ord-79b7a1e65273454498135b82beb8fe2c
출처 데이터셋: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08324239B2

반응 노트

불러오는 중…