1,2,3,4-Tetrahydroisoquinoline → HCID 86700212, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (25 mg, 50 μmol), N,N-dimethylacetamide and 1,2,3,4-tetrahydroisoquinoline (50 μL). The reaction was heated to 100° C. for 30 min. Then THF (1 mL), EtOH (absolute, 500 μL), and 5 M aq NaOH (500 μL) were introduced. The reaction was heated for another 30 min at 100° C. The reaction was cooled to 23° C., and filtered (0.45 micron teflon syringe filter). The filtrate was purified by reverse phase HPLC, eluting by 5-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+: calc'd for C29H29ClN2O3S: 521.2, 523.2 (M+H+); Found: 521.2, 523.2 (M+H+). 1H NMR (400 MHz, CD3OD): δ 7.71-7.47 (m, 4H), 7.38 (s, 1H), 7.30-7.22 (m, 4H), 5.17 (s, 1H), 4.79 (s, 2H), 3.84 (t, J=6.0 Hz, 2H), 3.09 (t, J=6.0 Hz, 2H), 2.54 (s, 3H), 0.96 (s, 9H).

Provenance & Evidence