Diethylamine → HCID 178463999, compound

Participants

Reaction Steps

A solution of toluene-4-sulfonic acid 3-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propyl ester (0.080 mg, 0.15 mmol) and diethylamine (0.45-0.75 mmol) in THF (10 mL) was stirred at 90° C. for about 2 hours in a sealed tube. After cooling to ambient temperature the reaction mixture was solvent evaporated. It was dissolved in ethyl acetate and washed twice with aqueous sodium bicarbonate. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was dissolved in methanol and chloroform, and ethereal hydrochloride was added. The mixture was concentrated and dried in vacuo at 80° C. for 17 hours. Diethyl-{3-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propyl}-amine hydrochloride was a tan foam (69.9 mg, 98.3%); Mass Spectrum (+EI, [M+H]+) m/z 438. 1HNMR (500 MHz, DMSO-d6): δ14.13-14.11 (br, 1H), 9.59-9.63 (br, 1H), 8.75 (d, 1H, J=8.42 Hz), 8.51 (dd, 1H, J=7.44 Hz and 1.10 Hz), 8.27 (d, 1H, J=8.29 Hz), 8.03-8.05 (m, 1H), 7.70-7.74 (m, 1H), 7.52-7.64 (m, 3H), 7.05-7.11 (m, 2H), 4.10 (t, 2H, J=5.98 Hz), 3.11-3.25 (m, 6H), 2.09-2.24 (m, 2H), 1.18 ppm (t, 6H, J=7.20 Hz).

Provenance & Evidence