Reaktion #612465

Reaktionsgleichung

Et2O

hydrazine

2-[(cis)-4-(7-morpholinoquinoxalin-5-yl)oxycyclohexyl]isoindoline-1,3-dione

→

compound 1030

(cis)-4-((7-morpholinoquinoxalin-5-yl)oxy)cyclohexanamine

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe precipitates were filtered off
2. 2
   Einengenthe filtrate concentrated under reduced pressure
3. 3
   workup.ADDITIONthe residue treated with DCM (30 mL)
4. 4
   Sonstigeany remaining solids removed by filtration
5. 5
   EinengenThe filtrate was concentrated under reduced pressure

Vorschrift

As shown in step 9-iii of Scheme 9, to a suspension of 2-[(cis)-4-(7-morpholinoquinoxalin-5-yl)oxycyclohexyl]isoindoline-1,3-dione (2.3 g, 5.02 mmol) in MeOH (25 mL) was added hydrazine (321 mg, 315 μL, 10.0 mmol) and the reaction mixture stirred for 18 hours at RT, over which time the initial suspension became homogenenous followed by the appearance of a precipitate. Et2O (30 mL) was added and the reaction mixture stirred an additional 30 minutes. The precipitates were filtered off, the filtrate concentrated under reduced pressure, the residue treated with DCM (30 mL), and any remaining solids removed by filtration. The filtrate was concentrated under reduced pressure to provide (cis)-4-((7-morpholinoquinoxalin-5-yl)oxy)cyclohexanamine (compound 1030), which was used as is in subsequent reactions: 1H-NMR (300 MHz, CDCl3) δ 8.69 (d, J=1.9 Hz, 1H), 8.62 (d, J=1.9 Hz, 1H), 6.95 (d, J=2.5 Hz, 1H), 6.90 (d, J=2.5 Hz, 1H), 5.00-4.67 (m, 3H), 4.03-3.81 (m, 4H), 3.49 (s, 1H), 3.43-3.25 (m, 4H), 2.88 (q, J=6.2 Hz, 2H), 2.36-1.96 (m, 6H).

Quelle