Bis(cyclohexylmethyl)amine → HCID 44469127, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (8R)-9-allyl-8-(3,5-difluorophenyl)-8-methyl-6,9-diazaspiro[4.5]decan-10-one (84 mg, 0.262 mmol), (2R)-6-bromo-2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-carbonitrile (98 mg, 0.288 mmol, described in Intermediate 26) and N,N-dicyclohexylmethylamine (0.0612 mL, 0.288 mmol) in degassed DMA (1.7 mL) at ambient temperature was added bis(tri-t-butylphosphine)palladium (44.2 mg, 0.087 mmol). The reaction mixture was heated at 120° C. for 18 h, cooled, and filtered through a plug of Celite, washing with EtOAc. The filtrate was concentrated in vacuo and the residue was first purified by HPLC using reverse phase C18 column, eluting with a gradient of H2O:CH3CN:CF3CO2H—65:35:0.1 to 45:55:0.1, then with preparative thin layer chromatography, eluting with a gradient of EtOAc:hexanes—50:50 to 70:30, to give the title compound. MS: m/z=580 (M+1). HRMS: m/z=580.2542 (M+1); calculated m/z=580.2519 (M+1) for C34H31F2N5O2.

Provenance & Evidence