Hydrogen Bromide → HCID 59262865, compound

Participants

Reaction Steps

4-[2-(3-Piperidin-1-yl-phenylamino)-thieno[2,3-h]quinazoline-8-carbonyl]-piperazine-1-carboxylic acid benzyl ester (205 mg, 0.34 mmol) was dissolved in dry DCM (4 mL) and HBr (2 mL, 33wt % solution in AcOH) added. The resultant mixture was stirred at room temperature for 0.5 hours and concentrated under reduced pressure. The yellow gum obtained was partitioned between Et2O and dilute HCl. The aqueous layer was extracted with Et2O (1×10 mL). The aqueous layer was then basified with saturated Na2CO3 and extracted with DCM (3×10 mL). The DCM organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The brown gum obtained was redissolved in DCM, silica (˜5 mL) added and concentrated under reduced pressure. The solid obtained was subjected to column chromatography (10% MeOH in DCM, ˜100 mL silica) to give a bright yellow solid. This solid was triturated with Et2O, filtered and washed with Et2O (3×5 mL) and pentane (3×5 mL) to give a yellow powder (96.4 mg, 60% yield). MS (ES+) 473, (ES−) 472. δH (CDCl3) 1.5-1.9 (6H, m), 2.9-3.1 (4H, m), 3.2-3.3 (4H, m), 3.8-3.9 (4H, m), 6.7 (1H, m), 7.2-7.3 (3H, m), 7.4 (1H, s), 7.6-7.7 (3H, m), 8.2-8.3 (1H, s), 9.1 (1H, s)

Provenance & Evidence