1-(8-Methyl-8-azabicyclo[3.2.1]octan-3-yl)-1H-indol-5-amine → HCID 178479854, compound

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Reaction Steps

Compound 85 (52 mg, 0.2036 mmol) is charged to a small, argon purged flask fitted with a magnetic stir bar. Anhydrous ethanol (5 mL) and thiophene-2-carboximidothioic acid methyl ester hydroiodide (87.1 mg, 0.3056 mmol) are added to the flask and the reaction was stirred under argon at ambient temperature for 23 hours, at which time the solvent was evaporated and the residue was purified via chromatography on silica gel (methanol:CH2Cl2, 1:9 to 2M NH3 in methanol:CH2Cl2, 5:95) to yield a pale yellow residue, 86 (77 mg, 100%). 1H NMR (major isomer-MeOD) δ 1.81-1.89 (m, 2H), 2.07-2.14 (m, 2H), 2.23-2.31 (m, 2H), 2.48 (s, 3H), 2.69-2.79 (m, 2H), 3.49-3.59 (m, 2H), 4.51-4.61 (m, 1H), 6.58 (d, 1H, J=3.3 Hz), 7.13 (dd, 1H, J=8.7, 1.9 Hz), 7.31-7.34 (m, 1H), 7.54-7.57 (m, 2H), 7.61 (d, 1H, J=3.5 Hz), 7.94-7.97 (m, 2H); ESI-MS (m/z, %): 365 (MH+, 15%), 183 (M++doubly charged, 100%); ESI-HRMS calculated for C21H25N4S (MH+): 365.1794, observed: 365.1784.

Provenance & Evidence