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. Author manuscript; available in PMC: 2020 Feb 14.
Published in final edited form as: J Med Chem. 2019 Jan 3;62(3):1502–1522. doi: 10.1021/acs.jmedchem.8b01662

Scheme 1.

Scheme 1.

Synthesis of (N)-methanocarba derivatives bearing typical A1AR-enhancing groups at the N6 and C2 positions with and optionally substituted at the 5′ position with chloro or an aryl thioether. Reagents and conditions: (i) R1NH2, DIPEA, 2-propanol, rt; (ii) TBAF, THF, rt; (iii) 10% TFA, MeOH, 70 oC; (iv) SOCl2, pyridine, CH3CN, −5 oC-rt (v) 2-F-PhSH, NaH, DMF, 0 oC-rt.