Piperazine → Isoloxapine

Temperatur

130 °C

A mixture of 8-chloro-10H-dibenzo[b,f][1,4]oxazepin-11-one (189JO29C) (30 mg, 0.069 mmol) and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (29 mg, 0.040 mmol) in toluene (2 mL) was heated in a capped tube using microwave assisted heating (130° C., 20 minutes). The reaction mixture was cooled to room temperature and MeI (38 μL, 0.29 mmol) was added and the resulting mixture was heated in capped tube using microwave assisted heating (120° C., 20 minutes). The mixture was concentrated and the residue was taken up in pyridine (2 mL) and piperazine (24 mg, 0.29 mmol) was added. The resulting mixture was heated in a capped tube at 130° C. over night then heated using microwave assisted heating (160° C., 30 minutes). The mixture was concentrated, diluted with EtOAc and washed with water. The organic phase was dried (Na2SO4), concentrated and flash chromatographed (SiO2, toluene:EtOAc:MeOH, 4:2:0-2:2:1) to give 8.9 mg of the title compound (189JO47). MS (ESI) 328 (MH+). Purity for MH+ (UV/MS) 98/93.

1. temperaturewas heated in a capped tube
2. temperatureThe reaction mixture was cooled to room temperature
3. temperaturethe resulting mixture was heated in capped tube
4. temperatureassisted heating (120° C., 20 minutes)
5. concentrationThe mixture was concentrated
6. temperatureThe resulting mixture was heated in a capped tube at 130° C. over night
7. temperaturethen heated
8. temperatureassisted heating (160° C., 30 minutes)
9. concentrationThe mixture was concentrated
10. additiondiluted with EtOAc
11. washwashed with water
12. dry with materialThe organic phase was dried (Na2SO4)
13. concentrationconcentrated
14. customflash chromatographed (SiO2, toluene:EtOAc:MeOH, 4:2:0-2:2:1)

ORD-Eintrag

ord-713dc12fd89243968ffcb168cfedfae7

Quelldatensatz

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07622461B2