Cesium carbonate → HCID 72714975, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Cs2CO3 (0.8 g, 2.43 mmol) in DMF (10 mL) were added 2-(benzyloxy)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one (0.3 g, 1.16 mmol) and (bromomethyl)cyclopropane (0.3 g, 2.34 mmol) at 0° C. The mixture was stirred at 150° C. for 18 hours. The mixture was diluted with ice-water and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in petroleum ether 0/10 to 1/10) to yield 2-(benzyloxy)-5-(cyclopropylmethyl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one (97 mg, 27% yield). C18H21N3O2. 1H NMR (400 MHz, CDCl3) δ ppm 0.27-0.39 (m, 2H), 0.51-0.66 (m, 2H), 1.01-1.14 (m, 1H), 2.28 (quin, J=6.7 Hz, 2H), 3.43 (d, J=7.3 Hz, 2H), 3.48 (t, J=6.4 Hz, 2H), 4.28 (t, J=7.0 Hz, 2H), 5.18 (s, 2H), 6.18 (s, 1H), 7.28-7.40 (m, 3H), 7.41-7.47 (m, 2H).

Provenance & Evidence