HCID 178514588, compound → HCID 178511145, compound

Participants

Reaction Steps

5-(3-Azido-propoxy)-3-(naphthalene-1-sulfonyl)-1H-indazole (0.763 g, 1.87 mmol) was dissolved in hot ethanol (125 mL). 10% Palladium on carbon (0.16 g) was added, and the reaction mixture was shaken and hydrogenated on the Parr apparatus for 2 hours, starting pressure 51 psi. Additional 1% Palladium on carbon (0.32 g) was added, and the reaction mixture was again hydrogenated on the Parr apparatus for 2 hours. It was then filtered over Celite and concentrated. The residue was purified by flash chromatography with 0.75% ammonium hydroxide/7.5% methanol in chloroform. The product was further purified by HPLC using a gradient of chloroform/methanol in heptane/TFA. 3-[3-(Naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propylamine as a light yellow foam (0.229 g, 32.1%) resulted. Methanol and ethereal hydrochloride were added. The mixture was concentrated and dried at 83° C. in vacuo for 12 hours to yield the hydrochloride as a light buff foam (0.235 g). Mass Spectrum (−EI, [M−H]−) m/z 380. 1HNMR (500 MHz, DMSO-d6): δ14.15 (s, 1H), 8.75 (d, 1H, J=8.67 Hz), 8.50-8.52 (m, 1H), 8.27 (d, 1H, J=8.30 Hz), 8.02-8.05 (m, 1H), 7.86 (s, br, 3H), 7.71-7.75 (m, 1H), 7.54-7.64 (m, 3H), 7.29 (d, 1H, J=2.20 Hz), 7.08-7.11 (m, 1H), 4.09 (t, 2H, J=6.10 Hz), 2.94-2.99 (m, 2H), 2.00-2.07 ppm (m, 2H). Elemental Analysis for C20H19N3O3S.1.00 mol HCl.0.40 mol H2O: Calcd: C, 56.51; H, 4.93; N, 9.88; Found: C, 56.21; H, 5.12; N, 9.56.

Provenance & Evidence