Dimethylformamide → HCID 86591494, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(2-bromo-8-methyl-1-thia-4,6,8a-triaza-as-indacen-5-yl)-N-(2-tert-butoxycarbonylaminoethyl)-amine (0.030 g, 0.070 mmol) in N,N-dimethylformamide (1 mL) was added copper(I) iodide (10.5 mgs), triethylamine (0.05 mL) and 2,2-dimethyl-but-3-yne (200 μL, 3.65 mmol). Argon was bubbled in the solution, then palladium(II) triphenylphosphine (13.8 mgs) was added and the mixture was stirred at 80° C. for 2 hours. The mixture was filtered on celite and the solvent was evaporated. The residue was purified by silica gel chromatography (50% ethyl acetate in hexane) to give N-(2-(hydroxy-pentyn-5-yl)-8-methyl-1-thia-4,6,8a-triaza-as-indacen-5-yl)-N-(2-tert-butoxycarbonylaminoethyl)-amine (0.021 g, 70%). This compound was dissolved in dichloromethane (1 mL) and treated with trifluoroacetic acid (0.2 mL) for 45 minutes. The solvents were evaporated and the residue was dissolved in methanol and treated with MP-carbonate resin. This mixture was stirred at room temperature for 2 hours, then filtered. The resin was washed with methanol and the filtrate was evaporated to give Compound 393 (0.014 g, 87%). NMR (DMSO-d6, 400 MHz) δ: 7.36 (2H, s), 7.27 (1H, s), 7.25 (1H, s), 3.51 (2H, q, J=5.6 Hz), 2.87 (2H, m), 2.65 (3H, s), 1.24 (9H, s). LRMS (ESI, m/z, M+H+) 327. HRMS for C17H21N5S calcd: 327.1518, found: 327.1516.

Provenance & Evidence