Methanol → HCID 58147264, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-[(5-isoxazol-3-yl-2-thienyl)sulfonyl]-1,2,3,4-tetrahydroisoquinoline-6-carboxylate obtained in step 1 in methanol (2 mL, 50 mmol) was added hydroxylamine hydrochloride (80 mg, 1 mmol) and potassium hydroxide (200 mg, 4 mmol). The reaction was left to stir for 2 hours at 80° C. Upon cooling to room temperature the solvent was removed in vacuo. The residue obtained was dissolved in DMSO (1 mL), the residual solids were removed by filtration and the resulting residue following evaporation was purified via reverse phase prep HPLC to afford the title compound as a white solid after lyophilization (Yield: 6.1%). LCMS (FA) ES+ 313; 1H NMR (400 MHz, d6 DMSO) δ: 0.87 (t, J=7.32, 7.46 Hz, 3H), 1.38 (q, J=7.545, 7.25, 7.57 Hz, 2H), 1.63 (q, J=7.76, 7.55, 7.80 Hz, 2H), 2.91 (t, J=5.29, 6.47 Hz, 2H), 4.44 (s, J=8.06, 7.81 Hz, 2H), 3.49 (t, 2H, 6.03 Hz, J=5.95), 4.44 (s, 2H), 7.24 (d, J=7.5 Hz, 1H), 7.56 (d, J=8.1 Hz, 1H), and 7.58 (s, 1H).

Provenance & Evidence