Water → HCID 71666208, Verbindung

HRID 929072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929072
[CH2:1]([C:4]1([S:7]([NH:10][C:11]2[C:19]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])=[C:18]([F:29])[C:14]3[N:15]=[N:16][S:17][C:13]=3[CH:12]=2)(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C[N+]1([O-])CC[O:34]CC1.[OH2:38]>C1COCC1.[Os](=O)(=O)(=O)=O>[OH:38][CH:2]([CH2:3][OH:34])[CH2:1][C:4]1([S:7]([NH:10][C:11]2[C:19]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])=[C:18]([F:29])[C:14]3[N:15]=[N:16][S:17][C:13]=3[CH:12]=2)(=[O:8])=[O:9])[CH2:5][CH2:6]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 89705457HCID 89705457, Verbindung

Produkt 1

HCID 71666208HCID 71666208, VerbindungAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-allyl-N-(4-fluoro-5-((2-fluoro-4-iodophenyl)amino)benzo[d][1,2,3]thiadiazol-6-yl)cyclopropane-1-sulfonamide (50 mg, 0.09 mmol) in THF (5 mL) was added N-methylmorpholine-N-oxide (12 mg, 0.09 mmol) followed by osmium tetraoxide (5 mg, 0.02 mmol) and water (0.5 mL). The resultant was stirred at room temperature overnight. The mixture was concentrated and then diluted with ethyl acetate. The organic layer was washed with water, saturated NaHCO3 (aq.) and brine sequentially, dried over Na2SO4, filtered and concentrated to give a residue, which was purified by flash chromatography on silica gel to give the product as white solid (30 mg, 56.5% yield). 1H NMR (400 MHz, CDCl3): δ 8.26 (s, 1H), 7.67-7.64 (d, 2H), 7.32 (m, 1H), 7.03 (s, 1H), 6.85 (s, 1H), 4.40-4.26 (m, 2H), 4.20-4.10 (m, 1H), 3.75-3.60 (m, 1H), 3.60-3.50 (m, 1H), 2.62-2.50 (m, 2H), 0.92-0.82 (m, 4H). MS APCI (+) m/z: 583.5, [M+H].

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with water, saturated NaHCO3 (aq.) and brine sequentially
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue, which
  8. customwas purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c83ac46f6827455b8938401f021d2d85
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290468B2

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