Potassium Carbonate → 2-(4-(2-(1-isopropyl-3-(methoxymethyl)-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)piperidin-1-yl)acetamide

Participants

Reaction Steps

A suspension of 2-(2-isopropyl-5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-8-piperidin-4-yl-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene trifluoroacetate salt (99 mg, 0.18 mmol) in THF (1.8 mL) was treated with 2-bromoacetamide (109 mg, 0.2 mmol) followed by potassium carbonate (56 mg, 0.41 mmol) and the reaction mixture stirred at RT before being diluted with DCM and water. The aqueous layer was extracted twice with DCM and the combined organic extracts washed with saturated aqueous sodium bicarbonate followed by brine then dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was dissolved in methanol, the solution cooled to 0° C. and treated with water to form a precipitate which was filtered off and washed with cold methanol/water to give a white solid. The solid was azeotroped with methanol then diethyl ether to give 308 as a white solid (38 mg, 43%). LCMS: RT=2.66 min, [M+H]+=480. 1H NMR 400 MHz (DMSO-d6) δ: 8.39 (1 H, d, J=8.32 Hz), 8.16 (1 H, s), 7.09-7.08 (1 H, m), 6.97 (1 H, s), 5.76-5.74 (1 H, m), 4.58 (4 H, d, J=14.42 Hz), 4.51 (2 H, s), 3.96 (2 H, s), 3.60 (2 H, d, J=11.71 Hz), 3.37 (3 H, s), 3.20 (2 H, m), 2.86 (1 H, m), 2.03 (4 H, m), 1.53 (6 H, d, J=6.57 Hz)

Provenance & Evidence