Sodium hydrosulfide → Tert-butyl (6-(3-isopropylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

HRID 219215

Reaktionsgleichung

Reaktionsgleichung von HRID 219215
[CH3:1][CH:2]([CH3:25])[C:3](=O)[C:4]#[C:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:13][N:14]=2)[N:11]=1.[NH2:26]OS(O)(=O)=O.C(=O)(O)[O-].[Na+].[SH-:37].[Na+]>O.O1CCOCC1>[CH:2]([C:3]1[CH:4]=[C:5]([C:6]2[CH:7]=[CH:8][C:9]3[N:10]([C:12]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:13][N:14]=3)[N:11]=2)[S:37][N:26]=1)([CH3:25])[CH3:1]

Komponenten

7

Edukt 4

HCID 28015Sodium hydrosulfideHCID 76284hydroxylamine-O-sulfonic acidHCID 516892Sodium BicarbonateHCID 57691360Tert-butyl (6-(4-methyl-3-oxopent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Produkt 1

HCID 57691285Tert-butyl (6-(3-isopropylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamateAusbeute 22,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

An aqueous mixture of tert-butyl (6-(4-methyl-3-oxopent-1-ynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (0.800 g, 2.33 mmol) and hydroxylamine-O-sulfonic acid (0.263 g, 2.33 mol) in water (8.0 mL) and 1,4-dioxane (8.0 mL) was stirred at 0° C. until complete consumption of the organic starting material was observed. The mixture was then carefully treated with solid sodium bicarbonate (0.196 g, 2.33 mmol), followed by treatment with 1.4 M aqueous sodium hydrosulfide (1.83 ml, 2.56 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was diluted with water (20 mL) and extracted with DCM (40 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The concentrated crude material was dissolved in minimal DCM and was purified via MPLC (eluting with 0-10% MeOH/NH4OH in DCM) to yield tert-butyl (6-(3-isopropylisothiazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (0.196 g, 22.5% yield) with 82% purity. MS (ESI pos. ion) m/z: 433.0 (M+H). Calc'd Exact Mass for C21H20N8OS: 432.51.

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionextracted with DCM (40 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. concentrationThe concentrated crude material
  7. dissolutionwas dissolved in minimal DCM
  8. customwas purified via MPLC (eluting with 0-10% MeOH/NH4OH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-979217b073eb4105a405364844328837
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198448B2

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