Reaktion #795467

Reaktionsgleichung

HATU

8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid

N′-isopropyl-hydrazinecarboxylic acid tert-butyl ester

DIPEA

→

title compound

Ausbeute 80.0%

N′-(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carbonyl)-N′-isopropyl-hydrazinecarboxylic acid tert-butyl ester

Ausbeute 80.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenbefore being concentrated in vacuo
2. 2
   workup.ADDITIONThe resultant residue was treated with water
3. 3
   Extraktionthen extracted with DCM (×3) before the combined organic extracts
4. 4
   Waschenwere washed with 10% citric acid
5. 5
   TrocknenThe organic layer was dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigeto give a brown oil
9. 9
   ExtraktionThe oil was extracted with diethyl ether (×5)
10. 10
    Einengenthe diethyl ether extracts concentrated in vacuo
11. 11
    Sonstigebefore being triturated with pentane

Vorschrift

To a mixture of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (5.20 g, 16.0 mmol) and N′-isopropyl-hydrazinecarboxylic acid tert-butyl ester (3.33 g, 19.1 mmol) in DMF (100 mL) at 0° C. was added DIPEA (6.93 mL, 39.9 mmol) followed by HATU (9.09 g, 23.9 mmol). The reaction mixture was stirred at RT for 72 h before being concentrated in vacuo. The resultant residue was treated with water then extracted with DCM (×3) before the combined organic extracts were washed with 10% citric acid, then saturated sodium bicarbonate solution followed by brine. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give a brown oil. The oil was extracted with diethyl ether (×5) and the diethyl ether extracts concentrated in vacuo before being triturated with pentane to give the title compound as a light brown solid (6.14 g, 12.7 mmol, 80%). LCMS: RT=5.02 min, [M+H]+=482/484.

Quelle