Benzylamine → HCID 178517969, compound

Participants

Reaction Conditions

Reaction Steps

To a 600 μL dried degassed toluene suspension of 27 mg (0.052 mmol) 8-[(6-bromopyridin-3-yl)methyl]-4-(cyclohexylamino)-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one (8-1, prepared in the same manner as Intermediate 5-3), 9 mg (0.094 mmol) sodium t-butoxide, 2 mg (0.003 mmol) racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP), and 2 mg (0.003 mmol) tris(dibenzylideneacetone)dipalladium (0) was added 29 μL (0.262 mmol) benzylamine. The reaction vessel was capped and warmed to 110° C. overnight. The clear toluene layer was decanted and the residue extracted (2× hot toluene). The combined organic extracts were concentrated to dryness in vacuo, the residue dissolved in 900 μL DMF and purified by preparative HPLC (5→95% CH3CN/H2O over 30 m, 0.05% added TFA, C18 PRO YMC 20×150 mm) to afford, after lyophilization, 8-{[6-(benzylamino)pyridinium-3-yl]methyl}-4-(cyclohexylamino)-1-(3-fluorophenyl)-2-oxo-1,3-diaza-8-azoniaspiro[4.5]dec-3-ene bis(trifluoroacetate) as a white fluffy solid. 1H NMR (CD3OD with K2CO3, 400 MHz): δ 7.70 (s, 1H), 7.34 (m, 5H), 7.23 (m, 2H), 7.08 (m, 3H), 6.47 (d, J=8.60 Hz, 1H), 4.49 (s, 2H), 3.77 (m, 1H), 3.28 (s, 2H), 2.68 (m, 2H), 2.12 (m, 4H), 2.00 (m, 4H), 1.80 (m, 2H), 1.68 (m, 1H), 1.33 (m, 5H). High resolution mass spec (FT/ICR): calc M+H=541.3086. found 541.3103

Provenance & Evidence