2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → HCID 53358258, compound

Participants

Reaction Conditions

Reaction Steps

To a Wheaton vial containing 3-(bromomethyl)biphenyl (22.2 mg, 0.090 mmol) and resin-supported BEMP (52 mg, 0.095 mmol) was added a solution of tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate (18 mg, 0.05 mmol) in acetonitrile (1 mL). The mixture was heated to 90° C. and shaken vigorously for two days. The reaction mixture was filtered, and the filtrate was concentrated. The crude product was taken in dichloromethane (0.5 mL) and trifluroacetic acid (0.5 mL) was added. The mixture was shaken for 4 hours at room temperature. It was concentrated and the residue was purified by prep HPLC to obtain the product (15.3 mg, 66% yield in two steps). 1H NMR (600 MHz, DMSO/CDCl3) δ 7.52-7.46 (m, 1H), 7.46-7.41 (m, 2H), 7.41-7.33 (m, 5H), 7.23 (d, J=7.4 Hz, 2H), 7.19-7.14 (m, 1H), 6.77 (d, J=9.1 Hz, 1H), 4.40 (s, 2H), 3.63 (s, 2H), 2.75 (t, J=6.4 Hz, 2H), 1.82 (t, J=6.5 Hz, 2H), 1.34 (s, 6H). LRMS [ESI, MH+] m/z calcd for C26H28NO5S 466.17, found 466.22.

Provenance & Evidence