Water → N-(benzo[d]thiazol-2-yl)-2-(4-chloro-5-formylthiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 1B (3.82 g, 10 mmol), 2,4-dichlorothiazole-5-carbaldehyde (1.82 g, 10 mmol), and Cs2CO3 (9.77 g, 30 mmol) in DMA (30 mL) was heated at 60° C. for 8 hours, cooled to rt and then poured into water (500 mL). The solid was collected by filtration and dried in a vacuum oven overnight (60° C.) to provide 4.2 g of the desired product (45A): 1H NMR (DMSO-d6): δ 12.66 (s, 1H), 9.69 (s, 1H), 8.00 (d, J=7.82 Hz, 1H), 7.77 (d, J=8.06 Hz, 1H), 7.73 (d, J=7.58 Hz, 1H), 7.40-7.49 (m, 3H), 7.33-7.36 (m, 1H), 5.04 (s, 2H), 3.82 (t, J=5.92 Hz, 2H), 3.11 (t, J=6.16 Hz, 2H). MS (ESI(+)): m/z 455 (M+H).

Provenance & Evidence