Reaktion #2270412

Reaktionsgleichung

hydrochloric acid

Triphenylphosphine

2-(tert-butyloxycarbonyl)piperazinylethanol

diethylazodicarboxylate

3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenol

→

title compound

Ausbeute 52.0%

1-(5-(1H-1,2,4-Triazol-5-yl)(1H-indazol-3-yl))-3-(2-piperazinylethoxy)benzene

Ausbeute 52.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring at ambient temperature for 4 h
2. 2
   Extraktionthe mixture was extracted with ether (3×)
3. 3
   workup.ADDITIONThe aqueous fraction was added to aqueous 6 N sodium hydroxide (25 mL)
4. 4
   ExtraktionThe solution was extracted with ethyl acetate (3×)
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe residue was purified by preparative HPLC (5-70% acetonitrile/water)
9. 9
   EinengenThe desired fractions were concentrated
10. 10
    workup.DISSOLUTIONdissolved in ethyl acetate
11. 11
    Waschenwashed with aqueous sodium bicarbonate
12. 12
    Trocknendried over anhydrous sodium sulfate
13. 13
    Filtrationfiltered
14. 14
    Sonstigeevaporated

Vorschrift

Triphenylphosphine (0.694 g, 2.65 mmol), tetrahydrofuran (2.12 mL), 2-(tert-butyloxycarbonyl)piperazinylethanol (0.610 g, 2.65 mmol) and diethylazodicarboxylate (0.418 mL, 2.65 mmol) were added to 3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenol (0.400 g, 0.662 mmol). The mixture was stirred at ambient temperature for 23 h and poured into aqueous 6N hydrochloric acid (25 mL). After stirring at ambient temperature for 4 h, the mixture was extracted with ether (3×). The aqueous fraction was added to aqueous 6 N sodium hydroxide (25 mL) and the pH adjusted to 11. The solution was extracted with ethyl acetate (3×) and the organic fractions were combined and dried over anhydrous sodium sulfate, filtered and evaporated. The residue was purified by preparative HPLC (5-70% acetonitrile/water). The desired fractions were concentrated, dissolved in ethyl acetate, washed with aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and evaporated to give the title compound (0.132 g, 52% yield) as the bis-trifluoroacetic acid salt. 1H NMR (D2O) δ 8.26 (s, 1H), 8.12 (s, 1H), 7.61 (d, 1H), 7.37 (d, 1H), 7.31 (m, 2H), 7.19 (m, 1H), 6.90 (m, 1H), 4.35 (m, 2H), 3.62 (m, 6H), 3.52 (m, 4H). ES-MS (m/z) 390 [M+1]+.

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