Methylamine → HCID 178482386, compound

Participants

Reaction Conditions

Reaction Steps

To a glass microwave reaction vessel was added cis-N1-(benzo[d]thiazol-2-yl)-N3-(3-chloropyrazin-2-yl)cyclobutane-1,3-diamine (Intermediate 81, 0.1952 g, 0.588 mmol), sodium tert-butoxide (0.226 g, 2.353 mmol, Sigma-Aldrich Chemical Company, Inc.), and BrettPhos precatalyst (7.05 mg, 8.82 mol, Strem Chemicals, Inc.), and methanamine solution, 2.0 M in THF (1.471 ml, 2.94 mmol, Sigma-Aldrich Chemical Company, Inc.) in dioxane (1.177 ml) to stir at 50° C. for 3 h. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (25 g), eluting with a gradient of 1% to 8% MeOH in CH2Cl2, to provide the title compound (110 mg, 0.337 mmol, 57.3% yield). LCMS showed product peak at 1.26 min (m+1=327.0). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.82-1.95 (m, 2 H) 2.80-2.91 (m, 5 H) 4.00-4.18 (m, 2 H) 6.31 (br. s., 1 H) 6.38 (d, J=6.06 Hz, 1 H) 7.03 (td, J=7.63, 1.17 Hz, 1 H) 7.20 (d, J=3.13 Hz, 1 H) 7.21-7.28 (m, 2 H) 7.41 (d, J=7.43 Hz, 1 H) 7.69 (dd, J=7.82, 0.78 Hz, 1 H) 8.36 (d, J=6.85 Hz, 1 H)

Provenance & Evidence