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Methyl morpholine oxide → 2-(2,3-Dihydroxypropyl)-5-[4-(1H-pyrazol-1-yl)benzyl]-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

HRID 449942
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 449942
[CH2:1]([N:4]1[C:28](=[O:29])[C:7]2=[N:8][N:9]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[CH:26][CH:25]=[N:24]4)=[CH:19][CH:18]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]2=[N:5]1)[CH:2]=C.C[N+]1([O-])CC[O:34]CC1.[C:38](=[O:41])(O)[O-].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[OH:34][CH:2]([CH2:38][OH:41])[CH2:1][N:4]1[C:28](=[O:29])[C:7]2=[N:8][N:9]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH:27]=[CH:26][CH:25]=[N:24]4)=[CH:21][CH:22]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]2=[N:5]1
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Komponenten

7

Edukt 3

HCID 82029Methyl morpholine oxideHCID 516892Sodium BicarbonateHCID 46897482Allyl-5-[4-(1H-pyrazol-1-yl)benzyl]-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

Produkt 1

HCID 468965082-(2,3-Dihydroxypropyl)-5-[4-(1H-pyrazol-1-yl)benzyl]-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318
Osmium Tetroxide
Katalysator
HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Allyl-5-[4-(1H-pyrazol-1-yl)benzyl]-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one [(Example 10), 600 mg, 1.57 mmol] was dissolved in tetrahydrofuran (65 mL) and water (65 mL), treated with 4-methylmorpholine 4-oxide (221 mg, 1.88 mmol, 1.2 equiv) and osmium tetroxide (50.0 μL, 0.160 mmol, 0.1 equiv). The mixture was stirred for 72 hours at ambient temperature, poured into sodium bicarbonate (200 mL, saturated aqueous) and extracted with ethyl acetate (2×150 mL) and chloroform (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The sodium sulfate was washed with a 1:1 mixture of methanol:chloroform (6×30 mL) and the filtrate was concentrated in vacuo. The residue was purified via silica gel gradient chromatography (100:0 to 85:15; dichloromethane:methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.30-8.26 (1H, m), 7.89 (1H, d, J=2.5 Hz), 7.72-7.67 (3H, m), 7.62-7.54 (3H, m), 7.39 (2H, d, J=8.4 Hz), 6.47-6.45 (1H, m), 5.88 (2H, s), 4.31 (2H, dd, J=5.3, 2.0 Hz), 4.18-4.13 (1H, m), 3.69-3.65 (2H, m), 3.49 (1H, d, J=5.8 Hz), 3.02 (1H, m); high resolution mass spectrometry (ES+) m/z 417.1684 [(M+H)+; calculated for C22H21N6O3: 417.1670].

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×150 mL) and chloroform (2×100 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe sodium sulfate was washed with a 1:1 mixture of methanol
  6. concentrationchloroform (6×30 mL) and the filtrate was concentrated in vacuo
  7. customThe residue was purified via silica gel gradient chromatography (100:0 to 85:15; dichloromethane:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-f9c15d08f7ba4c21bfb0420fd6f5173a
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08486946B2

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